tag:blogger.com,1999:blog-26383729522284792892012-01-27T22:36:09.956+07:00Chemistry, Drugs, Standar Procedures, ASTM, SNI, Free Download Link, Weapon and ExplosivesOverloadednoreply@blogger.comBlogger14981100tag:blogger.com,1999:blog-2638372952228479289.post-90487704802494657582012-01-26T10:44:00.000+07:002012-01-26T10:44:11.024+07:00

S. Gabriel, Ber. 20, 2224 (1887). Conversion of alkyl halides to primary amines by treatment with potassium phthalimide and subsequent hydrolysis: M. S. Gibson, R. W. Bradshaw, Angew. Chem. Int. Ed. 7, 919 (1968); B. Dietrich et al., J. Am. Chem. Soc. 103, 1282 (1981); O. Mitsunobu, Comp. Org. Syn. 6, 79-85 (1991). Modified conditions: S. E. Sen, S. L. Roach, Synthesis 1994, 756; M. N. Khan, J

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S. Gabriel et al., Ber. 21, 1049 (1888); W. Marckwald et al., ibid. 32, 2036 (1899); 33, 764 (1900); 34, 3544 (1901). Formation of ethylenimines (aziridines) by elimination of hydrogen halides from aliphatic vicinal haloamines with alkali. The method can be extended to the preparation of five- and six-membered cyclic amines: O. C. Dermer, G. E. Ham, Ethylenimine and Other Aziridines (Academic

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S. Gabriel, J. Colman, Ber. 33, 980, 996, 2630 (1900); 35, 2421 (1902). Formation of isoquinoline derivatives or substituted benzothiazines by the action of alkoxides on phthalimidoacetic or saccharin esters or ketones: C. F. H. Allen, Chem. Rev. 47, 284 (1950); H. Henecka, Houben-Weyl 8, 578 (1952); J. H. M. Hill, J. Org. Chem. 30, 620 (1965); W. C. Groutas et al., Biochem. Biophys. Res.

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C. I. Fujimoto, J. Am. Chem. Soc. 73, 1856 (1951); B. Belleau, ibid. 5441. Synthesis of cyclic α-substituted α,β-unsaturated ketones from enol lactones and Grignard reagents prepared from primary halides: Review: J. Weill-Raynal, Synthesis 1969, 49. Modified conditions: M. Aloui et al., Synlett. 1994, 115.

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P. Fritsch, Ann. 279, 319 (1894); W. P. Buttenberg, ibid. 327; H. Wiechell, ibid. 332. Carbene-mediated rearrangement of 1,1-diaryl-2-haloethylenes to diaryl acetylenes: G. Köbrich, Angew. Chem. Int. Ed. 4, 49 (1965); G. Köbrich, P. Buck in Acetylenes, H. G. Viehe, Ed. (Marcel Dekker, New York, 1969) pp 117, 131; G. Köbrich, Angew. Chem. Int. Ed. 11, 473 (1972); P. J. Stang, D. P. Fox, J. Org.

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C. Pomeranz, Monatsh. 14, 116 (1893); P. Fritsch, Ber. 26, 419 (1893); E. Schlittler, J. Müller, Helv. Chim. Acta 31, 914, 1119 (1948). Formation of isoquinolines by the acid-catalyzed cyclization of benzalaminoacetals prepared from aromatic aldehydes and aminoacetal; in the Schlittler-Müller modification the starting materials are benzyl amines and glyoxal semiacetal: M. J. Bevis et al.,

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K. Fries, G. Fink, Ber. 41, 4271 (1908); K. Fries, W. Pfaffendorf, ibid. 43, 212 (1910). Rearrangement of phenolic esters to o- and/or p-phenolic ketones with Lewis acid catalysts: A. H. Blatt, Org. React. 1, 342 (1942); A. Gerecs in Friedel-Crafts and Related Reactions, in vol. 3, Part 1; G. Olah, Ed. (Interscience, New York, 1964) pp 499-533; F. R. Jensen, G. Goldman in ibid. Part 2, p 1349

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P. Friedlaender, Ber. 15, 2572 (1882); P. Friedlaender, C. F. Gohring, ibid. 16, 1833 (1883). Base-catalyzed condensation of 2-aminobenzaldehydes with ketones to form quinoline derivatives: Reviews: R. H. Manske, Chem. Rev. 30, 124 (1942); C. C. Cheng, S. J. Yan, Org. React. 28, 37 (1982). Cyclic ketones containing S, or N: G. Kempter, S. Hirschberg, ibid. 98, 419 (1965); K. Rao et al., J.

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C. Friedel, J. M. Crafts, Compt. Rend. 84, 1392, 1450 (1877). The alkylation or acylation of aromatic compounds catalyzed by aluminum chloride or other Lewis acids: Reviews: C. C. Price, Org. React. 3, 1 (1946); G. A. Olah, Friedel-Crafts and Related Reactions, vol. 1-4 (Interscience, New York, 1963-1965); J. K. Groves, Chem. Soc. Rev. 1, 73 (1972); H. Heaney, Comp. Org. Syn. 2, 733-752, 753-

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A. W. Hofmann, Ber. 16, 558 (1883); 18, 5, 109 (1885); K. Löffler, C. Freytag, ibid. 42, 3427 (1909). Formation of pyrrolidines or piperidines by thermal or photochemical decomposition of protonated N-haloamines: M. E. Wolff, Chem. Rev. 63, 55 (1963); E. J. Corey, W. R. Hertler, J. Am. Chem. Soc. 82, 1657 (1960); R. Furstoss et al., Tetrahedron Letters 1970, 1263; S. Titouani et al.,

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A. Freund, Monatsh. 3, 625 (1882); G. Gustavson, J. Prakt. Chem. [2] 36, 300 (1887); H. B. Hass et al., Ind. Eng. Chem. 28, 1178 (1936). Formation of alicyclic hydrocarbons by the action of sodium (Freund reaction) or zinc (Gustavson reaction) on open chain dihalo compounds; 1,3-dichloropropane derived from the chlorination of propane obtained from natural gas is cyclized in the Hass

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E. Frankland, Ann. 126, 109 (1863); E. Frankland, B. F. Duppa, Ann. 135, 25 (1865). Formation of α-hydroxycarboxylic esters by reaction of dialkyl oxalates with alkyl halides in the presence of zinc, or amalgamated zinc, and acid: E. Krause, A. von Grosse, Die Chemie der metallorganischen Verbindungen (Berlin, 1937) p 225; K. Nützel, Houben-Weyl 13/2a, 741 (1973).

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E. Frankland, Ann. 71, 213 (1849); 85, 3641 (1853). Synthesis of zinc dialkyls from alkyl halides and zinc: Reviews: K. Nützel, Houben-Weyl 13/2a, 570 (1973); C. R. Noller, Org. Syn. coll. vol. II, 184 (1943).

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M. O. J. Forster, J. Chem. Soc. 107, 260 (1915). Formation of diazoketones from α-oximinoketones by reaction with chloramine: M. P. Cava, R. L. Litle, Chem. & Ind. (London) 1957, 367; W. Kirmse et al., Angew. Chem. 69, 106 (1957). Mechanism: J. Meinwald et al., J. Am. Chem. Soc. 81, 4751 (1959). Application to steroids: M. P. Cava, B. R. Vogt, J. Org. Chem. 30, 3776 (1965). Review and

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A. P. N. Franchimont, Ber. 5, 1048 (1872). Carboxylic acid dimerization to 1,2-dicarboxylic acids by treating α-bromocarboxylic acids with potassium cyanide followed by hydrolysis and decarboxylation: N. Zelinsky, Ber. 21, 3160 (1888); O. Poppe, ibid. 23, 113 (1890); R. C. Fuson et al., J. Am. Chem. Soc. 51, 1536 (1929); 52, 4074 (1930); 60, 1237 (1938); H. N. Rydon, J. Chem. Soc. 1936, 593; H

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I. Ugi, Angew. Chem. Int. Ed. 1, 8 (1962). The α-addition of an iminium ion and the conjugate base of a carboxylic acid to an isocyanide, followed by spontaneous rearrangement of the α-adduct to yield an α-aminocarboxamide derivative. Carbonyl compounds and amines, or their condensation products, serve as precursors to the iminium ion. The nature of the product depends primarily on the acid

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M. O. J. Forster, J. Chem. Soc. 75, 934 (1899); H. Decker, P. Becker, Ann. 395, 362 (1913). Formation of secondary amines by condensation of a primary amine with an aldehyde, addition of alkyl halide to the Schiff base, and subsequent hydrolysis: H. Glaser, Houben-Weyl 11/1, 108 (1957); F. Möller, ibid. p 956.

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J. Algar, J. P. Flynn, Proc. Roy. Irish Acad. 42B, 1 (1934); B. Oyamada, J. Chem. Soc. Japan 55, 1256 (1934). Alkaline hydrogen peroxide oxidation of o-hydroxyphenyl styryl ketones (chalcones) to flavonols via the intermediate dihydroflavonols: T. S. Wheeler, Record Chem. Progr. 18, 133 (1957); W. P. Cullen et al., J. Chem. Soc. C 1971, 2848. Mechanism: T. R. Gormley, et al., Tetrahedron 29,

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E. A. Flood, J. Am. Chem. Soc. 55, 1735 (1933). Formation of trialkylsilyl halides from hexaalkyldisiloxanes using concentrated sulfuric acid in the presence of ammonium chloride or fluoride, or by treatment of the intermediate silane sulfates with hydrogen chloride in the presence of ammonium sulfate H. W. Post, Silicones and Other Organic Compounds (New York, 1949) p 64; E. G. Rochow et al.,

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B. Tollens, R. Fittig, Ann. 131, 303 (1864); R. Fittig, J. König, ibid. 144, 277 (1867). Formation of alkylated aromatic hydrocarbons on coupling of an alkyl and an aryl halide with sodium: T. L. Kwa, C. Boelhouwer, Tetrahedron 25, 5771 (1969); B. J. Wakefield, Comp. Organometal. Chem. 7, 45 (1982); K. Miyoshi et al., Chemosphere 41, 819 (2000).

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F. Fischer, H. Tropsch, Ber. 56, 2428 (1923). Synthesis of hydrocarbons, aliphatic alcohols, aldehydes, and ketones by the catalytic hydrogenation of carbon monoxide using enriched synthesis gas from passage of steam over heated coke. The ratio of products varies with conditions. The high pressure Synthol process gives mainly oxygenated products and addition of olefins in the presence of cobalt

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E. Fischer, A. Speier, Ber. 28, 3252 (1895). Esterification of acids by refluxing with excess alcohol in the presence of hydrogen chloride or other acid catalysts: E. D. Hughes, Quart. Rev. 2, 110 (1948); A. J. Kirby in Comprehensive Chemical Kinetics vol. 10, C. H. Bamford, C. F. H. Tipper, Eds. (Elsevier, New York, 1972) p 57; E. K. Euranto in The Chemistry of Carboxylic Acids and Esters, S.

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E. Fischer, Ber. 17, 579 (1884). Formation of phenylhydrazones and osazones by heating sugars with phenylhydrazine in dilute acetic acid: E. G. V. Percival, Advan. Carbohyd. Chem. 3, 23 (1948); F. Micheel, Chemie der Zucker und Polysaccharide (Leipzig, 1956) p 54; W. Pigman, The Carbohydrates 1957, 452, 455; H. Simon et al., Fortschr. Chem. Forsch. 14, 451 (1970).

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E. Fischer, Ber. 8, 589 (1875). Formation of arylhydrazines by reduction of diazo compounds with excess sodium sulfite and hydrolysis of the substituted hydrazine sulfonic acid salt with hydrochloric acid. The process is a standard industrial method for production of arylhydrazines: G. H. Colemann, Org. Syn. coll. vol. I, 432 (1932); K. H. Saunders, The Aromatic Diazo-Compounds and Their

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E. Fischer, Ber. 29, 205 (1896). Condensation of equimolar amounts of aldehyde cyanohydrins and aromatic aldehydes in dry ether in the presence of dry hydrochloric acid: R. H. Wiley, Chem. Rev. 37, 410 (1945); J. W. Cornforth, R. H. Cornforth, J. Chem. Soc. 1949, 1028; J. W. Cornforth, Heterocyclic Compounds 5, 309 (1957); T. Onaka, Tetrahedron Letters 1971, 4391.

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E. Fischer, Ber. 36, 2982 (1903). Formation of polypeptides by treatment of an α-chloro or α-bromo acyl chloride with an amino acid ester, hydrolysis to the acid and conversion to a new acid chloride which is again condensed with a second amino acid ester, and so on. The terminal chloride is finally converted to an amino group with ammonia: C. L. A. Schmidt, The Chemistry of the Amino Acids

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O. Fischer, E. Hepp, Ber. 19, 2991 (1886). Rearrangement of secondary aromatic nitrosamines to p-nitrosoarylamines: H. J. Shine, Aromatic Rearrangements (Elsevier, New York, 1967) p 231; D. L. H. Williams in Comprehensive Chemical Kinetics vol. 13 (1972) p 454; S. Johan et al., J. Chem. Soc. Perkin Trans. II 1980, 165. Mechanism: D. L. H. Williams, ibid. 1982, 801. Applications: J. B. Kyziol,

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E. Fischer, F. Jourdan, Ber. 16, 2241 (1883); E. Fischer, O. Hess, ibid. 17, 559 (1884). Formation of indoles on heating aryl hydrazones of aldehydes or ketones in the presence of catalysts such as Lewis or proton acids: Reviews: B. Robinson, Chem. Rev. 63, 373 (1963); 69, 227 (1969); H. Ishii, Accts. Chem. Res. 14, 233-247 (1981); B. Robinson, The Fischer Indole Synthesis (Wiley, New York,

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H. Kiliani, Ber. 18, 3066 (1885); E. Fischer, ibid. 22, 2204 (1889). Extension of the carbon atom chain of aldoses by treatment with cyanide. Hydrolysis of the cyanohydrins followed by reduction of the lactone yields the homologous aldose: Reviews: C. S. Hudson, Advan. Carbohyd. Chem. 1, 2 (1945); T. Moury, Chem. Rev. 42, 239 (1948); L. Hough, A. C. Richardson, The Carbohydrates 1A, 118 (1972)

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A. Reissert, Ber. 38, 1603, 3415 (1905); J. M. Grosheintz, H. O. L. Fischer, J. Am. Chem. Soc. 63, 2021 (1941). Formation of 1-acyl-2-cyano-1,2-dihydroquinoline derivatives (Reissert compounds) by reaction of acid chlorides with quinoline and potassium cyanide; hydrolysis of these compounds yields aldehydes and quinaldic acid: Reviews: E. Mosettig, Org. React. 8, 220 (1954); W. E. McEwen, R. L.

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H. Finkelstein, Ber. 43, 1528 (1910). Reaction of alkyl halides with sodium iodide in acetone: C. K. Ingold, Structure and Mechanism in Organic Chemistry (Cornell Univ. Press, London, 2nd ed., 1969) p 435; J. Hayami et al., Tetrahedron Letters 1973, 385; S. Samaan, F. Rolla, Phosphorus and Sulfur 4, 145 (1978); W. B. Smith, G. D. Branum, Tetrahedron Letters 22, 2055 (1981). Modified

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R. J. Ferrier, J. Chem. Soc. Perkin Trans. I 1979, 1455. The stereochemically controlled conversion of hex-5-enopyranosides into cyclohexanones (inosose derivatives), catalyzed by mercury(II) salts, such that the 5-hydroxyl and the 3-substituent of the product are predominantly in a trans relationship: Stereochemical/mechanistic study: A. S. Machado et al., Carbohyd. Res. 233, C5 (1992); N.

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H. J. H. Fenton, Proc. Chem. Soc. 9, 113 (1893); J. Chem. Soc. 65, 899 (1894). Oxidation of α-hydroxy acids with hydrogen peroxide and ferrous salts (Fenton's reagent) to α-keto acids or of 1,2-glycols to hydroxy aldehydes: W. A. Waters in Organic Chemistry vol. 4, H. Gilman, Ed. (Wiley, New York, 1953) p 1157; G. Sosnovsky, D. Rawlinson in Organic Peroxides vol. 2, D. Swern, Ed. (

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O. Ruff, Ber. 31, 1573 (1898); 32, 550 (1899); H. J. H. Fenton, Proc. Chem. Soc. 9, 113 (1893). Shortening of the carbon chain of sugars by the oxidation of aldonic acids (as calcium salts) with hydrogen peroxide and ferric salts: W. Pigman, The Carbohydrates (Academic Press, New York, 1957) p 118; H. S. Isbell, M. A. Salam, Carbohyd. Res. 90, 123 (1981).

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A. L. Étard, Compt. Rend. 90, 534 (1880); Ann. Chim. Phys. 22, 218 (1881). Oxidation of an arylmethyl group to an aldehyde by treatment with chromyl chloride: W. H. Hartford, M. Darrin, Chem. Rev. 58, 1 (1958); H. O. House, Modern Synthetic Reactions (W. A. Benjamin, Menlo Park, California, 2nd ed., 1972) p 289; C. D. Nenitzescu et al., Rev. Roum. Chim. 14, 1543, 1553 (1969); I. I. Schiketanz

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A. E. Favorskii, J. Prakt. Chem. 88(2), 658 (1913); O. Wallach, Ann. 414, 296 (1918). Base-catalyzed rearrangement of α-haloketones to acids or esters. The rearrangement of α,α′-dibromocyclohexanones to 1-hydroxycyclopentanecarboxylic acids, followed by oxidation to the ketones is known as the Wallach degradation: Detailed experimental procedure: D. W. Goheen, W. R. Vaughan, Org. Syn. coll.

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D. A. van Dorp, J. F. Arens, Nature 160, 189 (1947); J. F. Arens et al., Rec. Trav. Chim. 68, 604, 609 (1949); O. Isler et al., Helv. Chim. Acta 39, 259 (1956). The preparation of alkoxyethynyl alcohols from ketones and ethoxyacetylene. In the Isler modification the tedious preparation of ethoxyacetylene is obviated by treating β-chlorovinyl ether with lithium amide to yield lithium

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A. E. Favorskii, J. Russ. Phys. Chem. Soc. 37, 643 (1905); Chem. Zentr. 1905, II, 1018; A. Babayan et al., J. Gen. Chem. (USSR) 9, 1631 (1939). Synthesis of acetylenic alcohols from ketones and terminal acetylenes in the presence of anhydrous alkali: A. W. Johnson, The Chemistry of Acetylenic Compounds vol. 1 (London, 1946) p 14; R. A. Raphael, Acetylenic Compounds in Organic Synthesis (New

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F. Feist, Ber. 35, 1537, 1545 (1902); E. Bénary, Ber. 44, 489, 493 (1911). Formation of furans from α-halogenated ketones or ethers and 1,3-dicarbonyl compounds in the presence of pyridine. When ammonia is used as the condensing agent, pyrrole derivatives are always formed as secondary products: T. Reichstein, H. Zschokke, Helv. Chim. Acta 14, 1270 (1931); 15, 268, 1105, 1112 (1932); R. C.

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A. W. Hofmann, Ber. 14, 659 (1881). Formation of an olefin and a tertiary amine by pyrolysis of a quaternary ammonium hydroxide: A. C. Cope, E. R. Trumbull, Org. React. 11, 317-493 passim (1960); K. W. Bentley, G. W. Kirby in Techniques of Organic Chemistry vol. IV, Pt. 2, A. Weissberger, Ed., Elucidation of Organic Structures by Physical and Chemical Methods (Wiley, New York, 2nd ed., 1973)

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D. A. Evans et al., J. Am. Chem. Soc. 101, 6120 (1979); 103, 2127 (1981). Highly enantioselective aldol condensation of the chiral N-acyl-oxazolidone via its dibutylboryl enolate with the appropriate aldehyde: Mechanistic studies: D. A. Evans et al., J. Am. Chem. Soc. 103, 3099 (1981). Synthetic applications: C. W. Phoon, C. Abell, Tetrahedron Letters 39, 2655 (1998); C. Pearson et al., ibid.

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J. Volhard, H. Erdmann, Ber. 18, 454 (1885). Synthesis of alkyl and aryl thiophenes by cyclization of disodium succinate or other 1,4-difunctional compounds (γ-oxo acids, 1,4-diketones, chloroacetyl-substituted esters) with phosphorus heptasulfide: L. H. Friedburg, J. Am. Chem. Soc. 12, 83 (1890); J. Chem. Soc. 58, 1400 (1890); R. Phillips, Org. Syn. coll. vol. II, 578 (1943); F. F. Blicke,

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B. Emmert, E. Asendorf, Ber. 72, 1188 (1939); B. Emmert, E. Pirot, ibid. 74, 714 (1941). Formation of pyridyldialkylcarbinols by condensation of ketones with pyridine or its homologs in the presence of aluminum or magnesium amalgam: C. H. Tilford et al., J. Am. Chem. Soc. 70, 4001 (1948); H. L. Lochti et al., ibid. 75, 4477 (1953); R. Abramovitch, R. Vinutha, J. Chem. Soc. C 1969, 2104; C. A.

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H. Emde, Ber. 42, 2590 (1909); Ann. 391, 88 (1912). Modification of the Hofmann degradation, q.v., method for reductive cleavage of the carbon-nitrogen bond by treatment of an alcoholic or aqueous solution of a quaternary ammonium halide with sodium amalgam. Also used as a catalytic method with palladium and platinum catalysts. The method succeeds with ring compounds not degraded by the Hofmann

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K. Elbs, E. Larsen, Ber. 17, 2847 (1884). Formation of polyaromatics (eg. anthracene) by intramolecular condensation of diaryl ketones containing a methyl or methylene substituent adjacent to the carbonyl group: L. F. Fieser, Org. React. 1, 129 (1942); G. N. Badger, B. J. Christie, J. Chem. Soc. 1956, 3435; N. P. Buu-Hoi, D. Lavit, Rec. Trav. Chim. 76, 419 (1957); Cl. Marie et al., J. Chem.

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K. Elbs, J. Prakt. Chem. 48, 179 (1893). Hydroxylation of monophenols to predominantely p-diphenols or oxidation of methyl-substituted aromatics by persulfates: S. M. Sethna, Chem. Rev. 49, 91 (1951); J. B. Lee, B. C. Uff, Quart. Rev. 21, 453 (1967); E. J. Behrman, Org. React. 35, 421-511 (1988); K. A. Parker, et al., J. Org. Chem. 52, 183 (1987); K. G. Watson, A. Serban, Aust. J. Chem. 48,

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J. Tscherniac, DE 134979; A. Einhorn et al., Ann. 343, 207 (1905); 361, 113 (1908). Introduction of the amidomethyl group into aromatic rings or activated methylene groups in the presence of sulfuric acid: Reviews: R. Schröter, Houben-Weyl 11/1, 795 (1957); Hellman Angew. Chem. 69, 463 (1957); H. E. Zaugg, W. B. Martin, Org. React. 14, 52 (1965); H. E. Zaugg et al., J. Org. Chem. 34, 11, 14 (

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P. Ehrlich, F. Sachs, Ber. 32, 2341 (1899). Formation of N-phenylimines by the base-catalyzed condensation of compounds containing active methylene groups with aromatic nitroso compounds; nitrones also may be formed F. Barrow, F. J. Thorneycroft, J. Chem. Soc. 1939, 769; A. McGookin, J. Appl. Chem. 5, 65 (1955); F. Bell, J. Chem. Soc. 1957, 516; D. M. W. Anderson, F. Bell, ibid. 1959, 3708; D

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F. Ullmann, Ann. 332, 38 (1904); F. Ullmann, P. Sponagel, Ber. 38, 2211 (1905). Copper-mediated coupling of aryl halides. Biaryl ether synthesis is similarly accomplished with aryl halides and phenols: P. E. Fanta, Chem. Rev. 38, 139 (1946); 64, 613 (1964); A. A. Moroz, M. S. Shvartsberg, Russ. Chem. Rev. 43, 679 (1974); P. E. Fanta, Synthesis 1974, 9; M. F. Semmelhack et al., J. Am. Chem. Soc.

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C. Glaser, Ber. 2, 422 (1869). Homocoupling of terminal alkynes catalyzed by cuprous salts in the presence of an oxidant and ammonium chloride: Synthetic applications: F. M. Menger et al., J. Am. Chem. Soc. 115, 6600 (1993); L. Guo et al., Chem. Commun. 1994, 243. This coupling may also be effected by cupric salts in pyridine and is often referred to as the Eglinton reaction. It is

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L. Gattermann, Ber. 31, 1149 (1898); Ann. 313, (1907). Preparation of phenolic aldehydes, phenol ethers or heterocyclic compounds by treatment of the aromatic substrate with hydrogen cyanide and hydrogen chloride in the presence of Lewis acid catalysts: W. E. Truce, Org. React. 9, 37 (1957); E. Baltazzi, L. I. Krimen, Chem. Rev. 63, 526 (1963); F. M. Aslam et al., J. Chem. Soc. Perkin Trans. I

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A. Pictet, A. Gams, Ber. 43, 2384 (1910). Formation of isoquinolines by cyclization of acylated aminomethyl phenyl carbinols or their ethers with phosphorus pentoxide in toluene or xylene: Reviews: W. M. Whaley, T. R. Govindachari, Org. React. 6, 151 (1951); W. Y. Gensler, Heterocyclic Compounds 4, 361 (1952); W. Herz, L. Tsai, J. Am. Chem. Soc. 77, 3529 (1955); A. A. Bindra et al.,

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P. Edman, Acta Chem. Scand. 4, 283 (1950). Cyclic degradation of peptides based on the reaction of phenylisothiocyanate with the free amino group of the N-terminal residue such that amino acids are removed one at a time and identified as their phenylthiohydantoin derivatives: S. Bösze et al., J. Chromatog. A 668, 345 (1994). Reviews: R. A. Laursen et al., Methods Biochem. Anal. 26, 201-284 (

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A. L. J. Beckwith et al., J. Am. Chem. Soc. 110, 2565 (1988); P. Dowd, S. C. Choi, Tetrahedron 45, 77 (1989). Free radical mediated ring expansions of haloalkyl β-ketoesters: Synthetic application: M. G. Banwell, J. M. Cameron, Tetrahedron Letters 37, 525 (1996); C. Wang et al., Tetrahedron 54, 8355 (1998).

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K. H. Dötz, Angew. Chem. Int. Ed. 14, 644 (1975). Three component cyclization of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex, an alkyne, and carbon monoxide, generating a Cr(CO)3 coordinated phenol: Solvent effects: K. S. Chan et al., J. Organometal. Chem. 334, 9 (1987). Methods development: S. Chamberlin et al., Tetrahedron 49, 5531 (1993); S. Chamberlin, W. D. Wulff,

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W. von E. Doering, P. M. LaFlamme, Tetrahedron 2, 75 (1958); US 2933544 (1960). Treatment of an olefin with bromoform and an alkoxide to yield the 1,1-dibromocyclopropane which reacts with an active metal to produce an allene: Reviews: M. Murray, Houben-Weyl 5/2a, 985 (1977); V. Nair, Comp. Org. Syn. 4, 1009-1012 (1991).

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O. Doebner, W. v. Miller, Ber. 16, 2464 (1883). Acid-catalyzed synthesis of quinolines from primary aromatic amines and α,β-unsaturated carbonyl compounds. When the latter are prepared in situ from two molecules of aldehyde or an aldehyde and methyl ketone, the reaction is known as the Beyer method for quinolines: F. W. Bergström, Chem. Rev. 35, 153 (1944); Y. Ogata et al., J. Chem. Soc. B

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O. Doebner, Ann. 242, 265 (1887); Ber. 20, 277 (1887); 27, 352, 2020 (1894). Formation of substituted cinchoninic acids from aromatic amines on heating with aldehydes and pyruvic acid: F. W. Bergström, Chem. Rev. 35, 156 (1944); R. C. Elderfield, Heterocyclic Compounds 4, 25 (1952); C. Centini, Rev. Soe. Venez. Quim. 7(5), 265 (1970), C.A. 74, 76301x (1971); G. E. Gream, A. K. Serelis, Aust.

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E. Knoevenagel Ber. 31, 2596 (1898); O. Doebner, Ber. 33, 2140 (1900). Condensation of aldehydes or ketones with active methylene compounds in the presence of ammonia or amines; the use of malonic acid and pyridine is known as the Doebner modification: Early reviews: J. R. Johnson, Org. React. 1, 210 (1942); G. Jones, ibid. 15, 204 (1967); H. O. House, Modern Synthetic Reactions (W. A.

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O. Dimroth, Ann. 364, 183 (1909); 459, 39 (1927). Rearrangement whereby exo- and endocyclic heteroatoms on a heterocyclic ring are translocated: D. J. Brown, J. S. Harper in Pteridine Chemistry, W. Pfleiderer, E. C. Taylor, Ed. (Macmillan, New York, 1964) pp 219-230; D. J. Brown in Mechanisms of Molecular Migrations vol. 1, B. S. Thyagarajan, Ed. (Wiley-Interscience, New York, 1968) p 209; D.

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K. von Auwers, K. Ziegler, Ann. 425, 217 (1921). Transformation of a 4,4-disubstituted cyclohexadienone into a 3,4-disubstituted phenol upon acid treatment: Reviews: C. J. Collins, et al., in The Chemistry of the Carbonyl Group, S. Patai, Ed. (Interscience, New York, 1966) pp 775-778; A. J. Waring, Adv. Alicyclic Chem. 1, 207 (1967); B. Miller in Mechanisms of Molecular Migrations vol. 1, B. S

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W. Dieckmann, Ber. 27, 102, 965 (1894); 33, 595, 2670, (1900); Ann. 317, 51, 93, (1901). Base-catalyzed cyclization of dicarboxylic acid esters to give β-ketoesters, the intramolecular equivalent of the Claisen condensation, q.v.: J. P. Schaefer, J. J. Bloomfield, Org. React. 15, 1-203 (1967); H. O. House, Modern Synthetic Reactions (W. A. Benjamin, Menlo Park, California, 2nd ed., 1972) pp

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D. B. Dess, J. C. Martin, J. Org. Chem. 48, 4155 (1983). Mild oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, employing the triacetoxyperiodinane (the “Dess-Martin Periodinane” reagent): Scope and limitations of fluoroalkyl-substituted carbinols as substrates: R. J. Linderman, D. M. Graves, J. Org. Chem. 54, 661 (1989). Methods development: D. B. Dess, J. C.

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N. J. Demjanov, M. Lushnikov, J. Russ. Phys. Chem. Soc. 35, 26 (1903); Chem. Zentr. 1903, 1, 828. Deamination of primary amines by diazotization to give rearranged alcohols. In the case of alicyclic amines, ring enlargement or contraction occurs: P. A. S. Smith, D. R. Baer, Org. React. 11, 157 (1960); H. Stetter, P. Goebel, Ber. 96, 550 (1963); R. Kotani, J. Org. Chem. 30, 350 (1965); V. Dave

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M. Tiffeneau et al., Compt. Rend. 205, 54 (1937). Rearrangement of β-amino alcohols upon diazotization with nitrous acid to give carbonyl compounds. Cyclic alcohols yield ring expanded or contracted products: Reviews: P. A. S. Smith, D. R. Baer, Org. React. 11, 157-188 (1960); H. Metzger, Houben-Weyl 10/4, 233 (1968); D. J. Coveney, Comp. Org. Syn. 3, 781-782 (1991). W. E. Parham, C. S.

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You may update your status on facebook by sending kungfuchem contents automatically. By using this cool facebook apps. Here are the steps 1. Login to your facebook account 2. point to this address 3. Authorize the apps (allow) 4. Fill this form to activate     a. add feed     b. on "feed url" paste this link         http://kungfuchem.blogspot.com/feeds/posts/default     c. on " source name" you

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R. Criegee, Ber. 64, 260 (1931). Oxidative cleavage of vicinal glycols by lead tetraacetate: Reviews: R. Criegee in Newer Methods of Preparative Organic Chemistry vol. 1 (Interscience, New York, 1948) pp 12-20; H. O. House, Modern Synthetic Reactions (W. A. Benjamin, Menlo Park, California, 2nd ed., 1972) pp 359-387; K. W. Bentley in Elucidation of Organic Structures by Physical and Chemical

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H. Kolbe, Ann. 69, 257 (1849). Formation of symmetrical dimers by the electrolysis of carboxylates (decarboxylative dimerization). The coupling of two distinct carboxylates yields unsymmetrical products: The dimerization of half-esters is known as the Crum Brown-Walker reaction: A. Crum Brown, J. Walker, ibid. 261, 107 (1891). Reviews: B. C. L. Weedon, Quart. Rev. 6, 380 (1952); A. K. Vijh,

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H. D. Dakin, Am. Chem. J. 42, 477 (1909). Replacement of the formyl or acetyl groups in phenolic aldehydes or ketones by a hydroxyl group by means of hydrogen peroxide: J. E. Leffler, Chem. Rev. 45, 385 (1949). Mechanistic studies: M. B. Hocking, et al., Can. J. Chem. 55, 102 (1977); eidem, ibid. 56, 2646 (1978); M. B. Hocking et al., J. Org. Chem. 47, 4208 (1982). Sodium percarbonate as

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L. Ruzicka, H. Meldahl, Helv. Chim. Acta 21, 1760 (1938); 22, 421 (1939). Originally discovered in 17β-hydroxy-20-ketosteroids, but thoroughly studied in the 17α-hydroxy-20-keto series, this reaction involves an acid- or base-catalyzed acyloin rearrangement which yields a 6-membered D-ring: R. B. Turner, J. Am. Chem. Soc. 75, 3484 (1953); D. K. Fukushima et al., ibid. 77, 6585 (1955); N. L.

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Eastwood Reaction (Eastwood Deoxygenation) G. Grank, F. W. Eastwood, Aust. J. Chem. 17, 1392 (1964). Stereospecific conversion of vicinal diols into olefins: Review: E. Block, Organic Reactions 30, 478-491 (1984). Cf. Corey-Winter Olefin Synthesis.

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P. K. Dutt, H. R. Whitehead, A. Wormall, J. Chem. Soc. 119, 2088 (1921); P. K. Dutt, ibid. 125, 1463 (1924). Preparation of diazoaminosulfinates by reaction of diazonium salts with aryl- or alkylsulfonamides followed by alkaline hydrolysis to yield the corresponding sulfinic acid of the sulfonamide, and the azide: H. Bretschneider, H. Rager, Monatsh. 81. 970 (1950); I. G. Laing, Rodd's

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E. Frankland, Ann. 126, 109 (1863); E. Frankland, B. F. Duppa, Ann. 135, 25 (1865). Formation of α-hydroxycarboxylic esters by reaction of dialkyl oxalates with alkyl halides in the presence of zinc, or amalgamated zinc, and acid: E. Krause, A. von Grosse, Die Chemie der metallorganischen Verbindungen (Berlin, 1937) p 225; K. Nützel, Houben-Weyl 13/2a, 741 (1973).

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J. C. Duff, E. J. Bills, J. Chem. Soc. 1932, 1987; 1934, 1305; 1941, 547; 1945, 276. Formylation of phenols or aromatic amines with hexamethylenetetramine in the presence of an acidic catalyst. Ortho-substitution is usual; however in the presence of anhydrous trifluoroacetic acid (TFA) regioselective ortho and para substitutions are observed. L. N. Ferguson, Chem. Rev. 38, 230 (1946); Y. Ogata

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M. Delépine, Compt. Rend. 120, 501 (1895); 124, 292 (1897). Preparation of primary amines by reaction of alkyl halides with hexamethylenetetramine followed by acid hydrolysis of the formed quaternary salts: S. J. Angyal, Org. React. 8, 197 (1954); Y. Basace et al., Bull. Soc. Chim. France 1971, 1468. Synthetic applications: S. N. Quessy et al., J. Chem. Soc. Perkin Trans. I 1979, 512; S.

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P. de Mayo et al., Proc. Chem. Soc. London 1962, 119; P. de Mayo, H. Takeshita, Can. J. Chem. 41, 440 (1963). Synthesis of 1,5-diketones by photoaddition of enol derivatives of 1,3-diketones to olefins, followed by a retro-aldol reaction, q.v.: P. de Mayo, Accts. Chem. Res. 4, 49 (1971); H. Meier, Houben-Weyl 4/5b, 924 (1975); W. Oppolzer, Pure Appl. Chem. 53, 1189 (1981). Intramolecular

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G. Darzens, Compt. Rend. 150, 707 (1910); C. D. Nenitzescu, I. P. Cantuniari, Ann. 510, 269 (1934); C. D. Nenitzescu, C. Cioranescu, Ber. 69, 1820 (1936). Acylation of olefins with acid chlorides or anhydrides catalyzed by Lewis acids. When performed in the presence of a saturated hydrocarbon the product is the saturated ketone: G. A. Olah, Friedel-Crafts and Related Reactions vol. 1 (

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G. Darzens, Compt. Rend. 139, 1214 (1904); 141, 766 (1905); 142, 214 (1906). Formation of α,β-epoxy esters (glycidic esters) by the condensation of aldehydes or ketones with esters of α-haloacids; the corresponding thermally unstable glycidic acids yield aldehydes or ketones on decarboxylation: M. S. Newman, B. J. Magerlein, Org. React. 5, 413 (1949); M. Ballester, Chem. Rev. 55, 283 (1955); H

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T. Curtius, Ber. 23, 3023 (1890); idem, J. Prakt. Chem. [2] 50, 275 (1894). Formation of isocyanates by thermal decomposition of acyl azides: The stepwise conversion of a carboxylic acid to an amine having one fewer carbon unit, via the azide and isocyanate, is referred to as the Curtius reaction: Synthetic applications: R. Lo Scalzo et al., Gazz. Chim. Ital. 118, 819 (1988); N. De Kimpe et

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G. Darzens, Compt. Rend. 183, 748 (1926). Cyclization of α-benzyl-α-allylacetic acid type compounds by moderate heating in concentrated sulfuric acid to yield tetralin derivatives: E. Bergmann, Chem. Rev. 29, 536 (1941); J. N. Chatterjea et al., Indian J. Chem. 20B, 264 (1981).

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G. Darzens, Compt. Rend. 139, 1214 (1904); 141, 766 (1905); 142, 214 (1906). Formation of α,β-epoxy esters (glycidic esters) by the condensation of aldehydes or ketones with esters of α-haloacids; the corresponding thermally unstable glycidic acids yield aldehydes or ketones on decarboxylation: M. S. Newman, B. J. Magerlein, Org. React. 5, 413 (1949); M. Ballester, Chem. Rev. 55, 283 (1955);

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H. D. Dakin, R. West, J. Biol. Chem. 78, 91, 745, 757 (1928). Reaction of α-amino acids with acetic anhydride in the presence of base to give α-acetamido ketones. The reaction occurs via the intermediate azlactone: Mechanism: R. Knorr, R. Huisgen, Ber. 103, 2598 (1970); W. Steglich, et al., Chem. Ber. 104, 3644 (1971); G. Holfe et al., Chem. Ber. 105, 1718 (1972); N. Allinger et al., J. Org.

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L. C. Craig, J. Am. Chem. Soc. 56, 231 (1934). Introduction of a halogen into the α-position of aminopyridines by treatment with sodium nitrite in hydrohalic acid followed by warming: H. S. Mosher, Heterocyclic Compounds 1, 515, 555 (1950); H. E. Mertel in The Chemistry of Heterocyclic Compounds, A. Weissberger, Ed., Pyridine and its Derivatives Part Two, E. Klingsberg, Ed. (Interscience, New

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W. H. Perkin, J. Chem. Soc. 23, 368 (1870). Formation of benzofuran-2-carboxylic acids and benzofurans by heating 3-halocoumarins with alkali: R. C. Elderfield, V. B. Meyer, Heterocyclic Compounds 2, 2, 5 (1951); K. Bowden, S. Battah, J. Chem. Soc. Perkin Trans. II 1998, 1604.

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J. W. Cornforth, The Chemistry of Penicillin (Princeton University Press, New Jersey, 1949) p 700. Thermal rearrangement of 4-carbonyl substituted oxazoles to their isomeric oxazoles via the postulated dicarbonyl nitrile ylides: Mechanistic study: M. J. S. Dewar, I. J. Turchi, J. Am. Chem. Soc. 96, 6148 (1974). Scope and limitations: eidem, J. Org. Chem. 40, 1521 (1975). Extension to the

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E. J. Corey, R. A. E. Winter, J. Am. Chem. Soc. 85, 2677 (1963). Synthesis of olefins from 1,2-diols and thiocarbonyldiimidazole. Treatment of the intermediate cyclic thionocarbonate with trimethylphosphite yields the olefin by cis-elimination: M. Tichy, J. Sicher, Tetrahedron Letters 1969, 4609; E. J. Corey, P. B. Hopkiss, ibid. 23, 1797 (1982); S. Kaneko et al., Chem. Pharm. Bull. 45, 43 (

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E. J. Corey, C. U. Kim, J. Am. Chem. Soc. 94, 7586 (1972). Oxidation of primary and secondary alcohols via their alkoxysulfonium salts. Upon the addition of base, the salt rearranges intramolecularly to aldehydes and ketones, respectively: Application to the synthesis of α-hydroxy ketones: E. J. Corey, C. U. Kim, Tetrahedron Letters 1974, 287; of 1,3-dicarbonyl compounds: S. Katayama et al.,

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A. C. Cope et al., J. Am. Chem. Soc. 62, 441 (1940). Highly stereoselective [3,3]-sigmatropic rearrangement of 1,5-dienes; “all-carbon” equivalent of the Claisen rearrangement, q.v.: When R = OH, the transformation is referred to as the oxy-Cope rearrangement: J. Berson, M. Jones, ibid. 86, 5019 (1964). Reviews: S. J. Rhodds, N. R. Raulins, Org. React. 22, 1-252 (1975); S. R. Wilson, ibid.

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A. C. Cope et al., J. Am. Chem. Soc. 71, 3929 (1949); idem et al., ibid. 75, 3212 (1953). Formation of an olefin and a hydroxylamine by pyrolysis of an amine oxide: Early reviews: C. H. DePuy, R. W. King, Chem. Rev. 60, 448 (1960); A. C. Cope, E. R. Trumbull, Org. React. 11, 317-493 passim (1960). Synthetic application: E. Tojo et al., Heterocycles 27, 2367 (1988). Mechanistic study: R. D.

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T. Sandmeyer, Ber. 17, 1633, 2650 (1884); L. Gattermann, Ber. 23, 1218 (1890); G. Körner, A. Contardi, Atti Accad. nazl. Lincei 23 II, 464 (1914), C.A. 9, 1478 (1915). Substitution of diazonium groups in aromatic compounds by halo or cyano groups in the presence of cuprous salts (Sandmeyer reaction), copper powder and hydrochloric or hydrobromic acid (Gattermann reaction) or cupric salts (

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M. Conrad, L. Limpach, Ber. 20, 944 (1887); 24, 2990 (1891). Thermal condensation of arylamines with β-ketoesters followed by cyclization of the intermediate Schiff bases to 4-hydroxyquinolines: R. H. Manske, Chem. Rev. 30, 121 (1942); R. H. Reitsema, ibid. 43, 47 (1948); H. Henecka, Chemie der Beta Dicarbonylverbindungen (Berlin, 1950) p 307; R. C. Elderfield, Heterocyclic Compounds 4, 30 (

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K. Alder et al., Ber. 76, 27 (1943). The addition of an alkene having an allylic hydrogen (ene) to a compound containing a multiple bond (enophile) to form a new bond between two unsaturated termini, with an allylic shift of the ene double bond, and transfer of the allylic hydrogen to the enophile. The mechanism is related to that of the Diels-Alder reaction, q.v.: Lewis acid-promoted

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G. Wittig, U. Schöllkopf, Ber. 87, 1318 (1954); G. Wittig, W. Haag, ibid. 88, 1654 (1955). Alkene formation from carbonyl compounds and phosphonium ylides, proceeding primarily through the proposed betaine and/or oxaphosphetane intermediates. The stereoselectivity can be controlled by the choice of ylide, carbonyl compound, and reaction conditions: When the ylide is replaced with a phosphine

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C. E. Castro, R. D. Stephens, J. Org. Chem. 28, 2163 (1963); R. D. Stephens, C. E. Castro, ibid. 3313; A. M. Sladkov et al., Bull. Acad. Sci. USSR, Div. Chem. Sci. 1963, 2043. The coupling of cuprous acetylides with aryl halides to yield arylacetylenes: Synthetic applications: J. D. Kinder et al., Synlett 1993, 149; J. Kabbara et al., Synthesis 1995, 299; M. S. Yu et al., Tetrahedron Letters

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Aluminon (qualitative test for aluminum). Aluminon is a trade name for the ammonium salt of aurintricarboxylic acid. Dissolve 1 g of the salt in 1L of distilled water. Shake the solution well to insure thorough mixing. Bang’s reagent (for glucose estimation). Dissolve 100 g of K2CO3, 66 g of KCl and 160 g of KHCO3 in the order given in about 700 mL of water at 30°C. Add 4.4 g of CuS04 and

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For each reagent listed, the last column of this table gives the mass in grams which is contained in a solution whose amount-of-substance concentration divided by the equivalence factor of the compound equals 0.1 mol/L. The equivalence factor given refers to the most common reactions of the reagent. In the older literature such a solution is often called a “decinormal solution” (0.1 N).

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For each compound listed, the last column of this table gives the mass in grams which is contained in 1 liter of a solution whose amount-of-substance concentration divided by the equivalence factor of the compound equals 0.1 mol/L. In the older literature such a solution is often referred to as a “decinormal solution” (0.1 N). Reference: Compendium of Analytical Nomenclature (IUPAC), Pergamon

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The solubilities of amino acids in water are highly variable. Besides the extremely soluble proline, hydroxyproline, glycine and alanine are also quite soluble. Other amino acids  are significantly less soluble, with cystine and tyrosine having particularly low solubilities. Addition of acids or bases improves the solubility through salt formation. The presence of other amino acids, in general,

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Alanine was isolated from silk fibroin by Weyl in 1888. It is present in most proteins and is particularly enriched in silk fibroin (35%). Gelatin and zein contain about 9% alanine, while its content in other proteins is 2–7%. Alanine is considered nonessential for humans. Arginine was first isolated from lupin seedlings by Schulze and Steiger in 1886. It is present in all proteins at an average

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There are a number of ways of classifiying amino acids. Since their side chains are the deciding factors for intra- and intermolecular interactions in proteins, and hence, for protein properties, amino acids can be classified as: • Amino acids with nonpolar, uncharged side chains: e. g., glycine, alanine, valine, leucine, isoleucine, proline, phenylalanine, tryptophan and methionine. • Amino

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