经典有机化学反应.doc

Acetoacetic Ester CondensationL. Claisen and O. Lowman, Ber, 20, 651(1887)A. Geuther, Arch. Pharm. 106, 97(1863)Also see Claisen CondensationAcetoacetic Ester SynthesisD.J. Cram, G.S. Hammond, Organic Chemistry, p.260(New Yourk, 1959)S.O. Laweson, et al, Arkiv Keml, 17, 429(1961)L.F. Fieser and M. Fieser, Advanced Organic Chemistry, p.446(New York, 1961)Acyloin CondensationS.M. McElvain in Organic Reactions, Vol. 4, p. 256(New York, 1948); Stoll, Chimia 2, 217(1948); Prelog, J. Chem. Soc. 1950, 450; Sicher in Progress in Stereochemistry, De la Marc and Klyne, Eds, vol. 3, 202(Butterworth, 19520; Finley, Chem. Revs, 64, 573(1964);Adkins CatalystH. Adkins, Reactions of Hydrogen with Organic Compounds over Chromium Oxide and Nickel Catalysts, p12(Madison, Wisconsin, 1937)H. Adkins, et al, J. Am. Chem. Soc. 72, 2626(1950); Organic Synthesis, 36, 12(1956); 33,38(1953).Adkins-Peterson ReactionAir oxidation of methanol to formaldahyde over metal oxide catalysts.H. Adkins, W.R. Peterson,J. Am. Chem. Soc. 53,1512(1931)H. Hausdorfer in Ullmanns Enzyklopadie der technischen Chemie, 3rd ed., vol. 7(1956); p.622W. Kunz, H. Krauch, Chemiker-Zig, 82, 802(1958).Akabori Amino Acid Reactions1. Oxidize an alpha amino acid by heating with an oxidizing sugar.2. Reduce alpha amino acids and esters by sodium amalgam and ethanolic HCl to alpha amino aldehydes.S. Akabori, J. Chem. Soc. Japan, 52, 606(1931); Ber, 66, 143,151(1933); J. Chem. Soc. Japan, 64, 608(1943);3. Form alkamines by heating aromatic aldehydes with amino acids. No reaction observed with teriary amino groups. Example is pending E. Takagi, et al., J. Pharm. Soc. Japan, 71, 648(1951); 72,812(1952)A. Lawson, H.V. Motley, J. Chem. Soc., 1955, 1695A. Lawson, J. Chem. Soc. 1956, 307.Alder-Rickert RuleK. Alder, H.f. Ricker, Ann., 524, 180(1936)K. Alder in Newer Methods of Preperative Organic Chemistry, English, Ed. (Interscience, New York, 1948), p. 471A.C. Cope, A.C. Haven, Jr., F.L. Ramp, E.R. Trumbull, J. Am. Chem. Soc. 74, 4867(1952);Also see Diels Alder ReactionAldol CondensationA. A. Frost and R. G. Pearon, Kinetics and Mechanism, p 291 (New York, 1953)R. P. Bell and M. J. Smith, J. Chem. Soc. 1958, 1691V. Franzen, Reaktionsmechanismen I, 95 (Heidelberg, 1958)F. Klages, Lehrbuch der organischen Chemie II, 333 (Berlin, 1959)L. F. Fieser and M. Fieser, Advanced Organic Chemistry, p 456 (1961) Also see Claisen Condensation Algar-Flynn-Olyamada (AFO) ReactionJ. Algar and J. P. Flynn, Proc. Roy. Irish Acad. 42B, I (1934)B. Oyamada, J. Chem. Soc. Japan 55, 1256 (1934)Murakami, Irie, Proc. Imp. Acad. Japan 11, 229 (1935)Geissmann, Fukushima, J. Am. Chem. Soc. 70, 1686 (1948)Venkataraman in Zechmeister, Progress In the Chemistry of Organic Narural Products vo1. 17, p2 (1959)Review: Wheeler Recor, Chem. Progr. 18, 133 (1957). Also see Auwers SynthesisAllan-Robinson ReactionJ. Allan and R. Robinson, J. Chem. Soc. 125, 2192 (1924)Dyke et al., J. Org. Chem. 26, 2453 (1961)Seshandri in The Chemistry of Flavonoid Compounds, T. A. Geissman, Ed. (New York, 1962), p182Gripenberg, ibid., p 41l. Rahman, Nassim, J. Org. Chem. 27, 4215 (1962)Dreyer et al., Tetrahedron,20,2977(1964)Also see Kontanecki Acylation ; Baker-Venkataraman TransformationAllylic RearrangementL. Claisen, Ber. 45, 3157 (1912)G. W. Wheland, Resonance in Organic Chemistry, p 533 (New York, 1955)J. R. De Wolfe and W. G. Young, Chem. Revs. 56, 753 (1956)Also see Claisen Rearrangement Amadori RearrangementM. Amadori, Atti accad. nazl. Lincei. 2(6), 337(1925); 20,902(1926)M. Amadori, Atti accad. nazl. Lincei 9(6),68,226(1929); 23,3211,3443(1929)Hodge in Advances of Carbohydrate Chemistry vol. 10, p169 (1955)Pigman, The Carbohydrates, p422 (New York, 1957)Lemieux in P. de Mayo, Molecular Rearrangements pt. 2, p 753 (1964)Weygand, Ber. 73, 1259-1278 (1940)Isbell, Frusch, J. Org. Chem. 23, 1309 (1958)Micheel, Dijong, Ann. 658, 120 (1962)Also see: Claisen Rearrangement Andrussov OxidationL. Andrussov, Ber. 60, 2005(1927)Angew. Chem. 48, 593 (1935).E. Asendorf, W. Klempt, Ullmann Enzyklopadie der technischen Chemie 5, 635W. Kunz, H. Krauch, Chemiker Ztg. 83, 82 (1959)Ger. pats. 1,077,198 (1960), 1,100,600 (1960)Italian pat. 543,662 (1956)Molinari et al., J. Catalysis 4(3), 341(1965)A. A. Borisov and G. I. Skachkov, Kinetika i Kataliz 5(3), 496 (1964)Arens-van Dorp Synthesis; Isler Modification.D. A. van Dorp and J. F. Arens, Nature 160, 189 (1947)J. F. Arens, D. A. van Dorp and W. Graham, Rec. Trar,. Chitn. 68, 604, 609 (1949)O. Isler, M. Montavon, R. Ruegg and P. Zeltzer, Helv. Chim. Acta 39, 259 (1956) H. Heusser, K. Eichenberger and P. A. Plattner, Helv. Chim. Acta 33, 370 (1950)J.F. Arens in R. A. Raphael, E. C. Taylor, H. Wynberg, Advances in Organic Chemistry, vol. 2 (Interscience, New York, 1960), pp 117-212.Arndt-Eistert Synthesis.F. Arndt and B. Eistert, Ber. 68, 200 (1935)W. E. Bachmann and W. S. Struve, Organic Reactions 1, 38 (1942);B. Eistert, Newer Methods of Preparative Organic Chemistry, English Ed.,(New York, 1948), p545;A. L. Wilds, A. L. Meader, J. Org. Chem. 13, 763 (1948);H. Wotiz, S. N. Buco, J. Org. Chem. 20, 210 (1955);Kunz, Krauch, Chemiker-Ztg. 82, 868 (1958);J. L. Adelfang, G. H. Daub, J. Org. Chem. 23, 749 (1958).Also see: Wolff Rearrangement , Nierenstein Reaction Auwers Synthesis.K. v. Auwers et al., Ber. 41, 4233 (1908); 48, 85 (1915); 49, 809 (1916)K. v. Auwers and P. Pohl, Ann 405, 243 (1914)T. H. Minton and H. Stephen, J. Chem. Soc. 121, I598 (1922)J. Kalff and R. Robinson, J. Chem. Soc. 127, 1968 (1925)B. H. Ingham et al., J. Chem. Soc. 1931, 895B. G. Acharya et al., J. Chem. Soc. 1940, 817; R. S. Elderfield, Heterocyclic Compounds 2, 245(New York, 1951).Algar-Flynn-Olyamada(AFO)ReactionAza-Claisen Rearrangement.Diederich, M.; Nubbemeyer, U. Angew. Chem. 1995, 107, 1095; Int. Ed. Engl. 1995, 34, 1026zNubbemeyer, U., J. Org. Chem. 1996, 61, 3677Diederich, M.; Nubbemeyer, U., Chemistry, European J., 1996, 2, 894Ernst, B.; Gonda, J.; Jeschke, R.; Nubbemeyer, U.; hrlein, R.; Bellus, D., Helv. Chim. Acta, 1997, 80, 876Sudau, A.; Nubbemeyer, U. Angew. Chem. 1998, 110, 1178.Baeyer-Drewson Indigo SynthesisA. Baeyer, V. Drewson, Ber. 15, 2856(1882)K. Venkataraman, chemistry of Synthetic Dyes 2, 1008(New York, 1952)M. Sainsbury, Rodds Chemistry of Carbon Compounds IVB, 346,353(1977)J. R. McKee et al., J. Chem. Ed. 68, A242(1991)L. Fitjer et al., Tetrahedron 55, 14421(1999) Also see Algar-Flynn-Olyamada(AFO)Reaction Baeyer-Villiger RearrangementA. Baeyer, V. Villiger, Ber, 32,3625(1899); 23,858(1900)S.L.Friess, R. Pinson, J. Am. Chem. Soc. 74, 1302(1952)K. Mislow, J. Brenner, J. Am.Chem.Soc.75,2318(1953)W.A. Waters in H. Gilman, Organic Chemistry, vol 4,1169(John Wiley & Sons, New York, 1953)W. Sager, A. Duckworth, J.Am. Chem. Soc. 77, 188(1955)C.H.Hassall, Organic Reactions 9,73(1957)M.F.Hawthorne, W.D. Emmons, K.S. McCallum, J.Am.Chem.Soc 80,6393(1958)M.F. Hawthorne,W.D. Emmons,ibid,80,6398(1958)V. Franzen, Reaktionsmechanismen I p73-77(A. Huthig Verlag, Heidelberg, 1958)L.F.Fieser, M.Fieser, Advanced Organic Chemistry 427 (Reinhold, New York 1961)J.D.McClure, P.H. Williams, J. Org. Chem. 27,24,(1962)J.L. Mateos, H. Menchaca, ibid. 29,2026(1964)J.T.Pinhey, K.Schaffner, Tetrahedron Letters 1965,601J.C.Robertson, A. Swelim,ibid, 1967(30),2871Baekeland(Bakelite) ProcessA. von Bayeyer, Ber, 5, 280(1872)L. Lederer, J. Prakt. Chem(2), 50,223(1984)O. Manasse, Ber, 27,2409(1894)L.H. Baekeland Ind. Eng. Chem, I, 149(1909)J.F. Walker, Formaldehyde(New York, 1953) K.H. Meyer, H. Mark, Makcromoleculare Chemie(Liepzig,1950)Baker-Venkataraman TransformationW.Baker,J.Chem.Soc.1933,1381H.S. Mahal, K. Venkataraman, J. Chem.Soc. 1934,1767Wheeler et al Proc. Roy. Irish Acad. 24,291(1948)Allis, Weight, J.Chem.Soc. 1952, 3826Schmid, Banholzer, Helv. Chim, Acta 37,1706(1954)Reviews: Venkataraman in Zechmeister, Progress in the Chemistry of Organic Natural Products, vol. 17,p2(1959)Gripenberg in Geissman, Ed., The Chemistry of Flavonoid Compounds,p410(New York, 1962)Also see Allan-Robinson Reaction Bally-Scholl SynthesisO.Bally, Ber, 38,194(1905)O.Bally, R. Scholl, Ber, 44,1656(1911)H. Meerwein, J. Prakt. Chem. 97,235(1918)F.G.Baddar, F.L. Warren, J.Chem.Soc. 1938,401E.H.Rodd, Chemistry of Carbon Compounds IIIB,p1496(Elsevier, New York,1956)A.M.Lukin, Zh.Obschch. Khim,18,308(1948)T. Pfliegel, Chem. Prumysl 5,370(1955)Bamberger RearrangementE. Bamberger, Ber, 27,1347,1548(1894)H. J. Shine, Aromatic Rearrangements(Elsevier, New York, 1967) pp 182G. Kohnstam et al., J. Chem. Soc. Perkin Trans. II 1984, 423D. Johnston, D. Elder, J. Labelled Compd. Radiopharm. 25,1315(1988)Also see Bischler-Triazine Synthesis Bamberger Triazine SynthesisE.Bamberger, E.Wheelwright, Ber, 25,3201(1892)E.Bamberger, J.Lorenzen, Ber, 25,3539(1892)E. Bamberger, H. Witter, Ber, 26,2786(1893)E. Bamberger, R. Padova, E.Ormered, Ann. 446,260(1925)G. D. Parkes and B. C. Aldis, J. Chem. Soc. 1938E. Bamberger and J. Lorenzen, Ber. 25, 3539 (1892)E. Bamberger, R. Padova, and E. Ormered, Ann. 446, 260 (1925)R. A. Abramovitch and K. Schofield, J. Chem. Soc. 1955, 2326Bamford-Stevens ReactionW. R. Bamford and T. S. Stevens, J. Chem. Soc. 1952, 4735Powell, Whiting, Tetrahedron 7, 305 (1959)Friedman, Schechter, J. Am. Chem. Soc. 81, (1965)Wilt et al., J. Org. Chem. 40, 1052 (1965)Fischer et al., Ber. 98, 3236 (1965).Kaufman et al., J. Am. Chem. Soc. 87,935(1965) Barbier ReactionP. Barbier, C. R. Acad. Sci. 128, 110 (1899)D.P. Curran et al., Synlett 1992, 943-961. F. Hong et al., Chem. Commun. 1994,289K. Hafner et al., Eds.(Springer-Verlag, New York,1993) pp 183M. Kunishima et al., Chem. Pharm, bull. 42,2190 (1994)M. Kihara et al., Tetrahedron 48, 67(1992)Barbier-Wieland DegradationH. Wieland, Ber. 45, 484 (1912)P. Barbier and R. Locquin, Compt. Rend. 156, 1443 (1913)H. Wieland, O. Schlichting, and R. Jacobi, Z. Physiol. Chem. 161, 80 (1926)C. W. Shoppee, Ann. Repts. (Chem. Soc.,London) 44,184 (1947)W. Baker, R. F. Curtis, J. F. W. McOmie, L. W. Oliol, and V. Rogers, J. Chem. Soc. 1958, 1007Also see Gallagher-Hollander Degradation , Krafft Degradation , Miescher Degradation Bardhan-Senguph Phenanthrene Synthesis. J. C. Bardhan and S. C. Sengupta, J. Chem. Soc. 1932, 2520, 2798.R. P. Linstead, Ann. Repts. (Chem. Soc., London) 33, 319 (1936)L. F. Fieser and M. Fieser,Natural Products Related to Phenanthrene (New York, 1949), p 88W. B. Renfrow et al., J. Am. Chem. Soc. 73, 317 (1951).Bart Reaction (Scheller Modification)H. Bart, German Patent 250264 (1910)H. Bart, German Patent 254092 (1910)H. Bart, German Patent 264924 (1910)H. Bart, German Patent 268172 (1912)E. Scheller, British Patent 261026A. W. Ruddy et al., J. Am. Chem. Soc. 64, 828 (1942)C. F. Hamilton, J. F. Morgan, Org. React.2,415 (1944)G. O. Doak, H. G. Steinman, J. Am. Chem. Soc. 68, 1987 (1946)K. H. Saunders, Aromatic Diazo-Compounds and Their Technical Applications (London, 1949) p 330W. A. Cowdry, D.S. Davies, Quart. Rev. 6, 364 (1952)Barton Deoxygenation (Barton-McCombie Reaction)D. H. R. Barton, S. W. McCombie, Perkin Trans. 1, 1975, 1974M. Pereyre et al, Tin in Organic Synthesis (Butterworths, Boston, 1987)pp 84-96C. Chatgilialoglu, C. Ferreri, Res. Chem. Intermed. 19, 755-775 (1993)Barton Olefin Synthesis (Barton Kellogg Reaction)D.H.R. Barton et al., Chem. Commun. 1970, 1226R. M. Kellogg, S. Wassenaar, Tetrahedron Letters 1970, 1987R. M. Kellogg et al., Tetrahedron Letters, 1970, 4689D. H. R. Bartoln et al., Perkin Trans. 1, 1974, 1794A. P. Schaap, G. R. Faler, J. Org. Chem. 38, 3061(1973)L. K. Bee et al., J. Org. Chem. 40,2212(1975)M. D. Bachi et al., Tetrahedron Letters 1978, 4167Also see: McMurry Reaction Barton ReactionD. H. R. Barton, J. M. Beaton, L. E. Geller and M. M. Pechet, J. Am. Chem. Soc. 82, 2640(1960); 83, 4076 (1961).L. Nussbaum and C. H. Robinson, Tetrahedron, 17, 35 (1962); P. Gray, ibid. 18, 879 (1962)M.Akhtar and M. M. chet, J. Am. Chem. Soc. 86, 265 (1964); J. M. Erikson and D. L. Forbes in C.Djerassi, Steroid Reactions (Holden-Day, Francisco, 1963), pp 341, 343, 358, 364; T. Jen and M.E. Wolff, J. Org. Chem. 28, 1573 (1963) K. Heusler and J. KaIvoda, Angew. Chem. (Internatl.Ed. in Engl.) 3, 525 (1964); M. A. Khtar, D. H. R. Barton and P. G. Sammes, J. Am. Chem. Soc.86, 3394 (1964); R. A. Sneen and N. P. Matheny, ibid. 86, 5503 (1964).Baudisch Reaction Baudisch et al., Naturwissenschaften 27, 768, 769 (1939)Baudisch et al.,Science 92, 336 (1940)Baudisch et al.,J. Am. Chem. Soc. 63, 622 (1941)G. Cronheim J. Org. Chem. 12, 1, 7, 20 (1947)Konecny, J. Am. Chem. Soc. 77, 5748 (1955)Maruyama et al., Tettahedron Letters 1966, 5889.Baylis-Hillman ReactionA. B. Baylis, M.E.D. Hillman, Ger. pat. 2155113A. B. Baylis, M.E.D. Hillman, U.S. pat. 3743669 (1972, 1973)S. E. Drewes, G.H.P.Roos, Tetrahedron 44, 4653-4670(1988)Bechamp ReactionA. J. Bechamp, Compt. Rend. 56, 1172 (1863).P. Ehrlich and A. Bertheim, Ber. 40, 3292 (1907)H. P. Brown and C. S. Hamilton, J. Am. Chem. Soc. 56, 151 (1934)C. S. Hamilton and J. F. Morgan, Organic Reacrions II, pp 415, 428 (New York, 1944).Beckmann Rearrangement E. Beckmann, Ber. 19, 988 (1886)A. H. Blatt, Chem. Rev. 12, 215 (1933)B. Jones, Chem. Rev. 35, 335 (1944)F. D. Popp, W. E. McEwen, Chem. Rev. 58,370 (1958)A. F. Ferris, 1. Org. Chem. 25, 12 (1960)L. G. Donaruma and W. Z. Heldt, Organic Reactions 11, 1-156 (1960)R. K. Hill, O. T. Chortyk, J. Am. Chem. Soc. 84, 1064 (1962)R. T. Conley, J. Org. Chem. 28, 278 (1963).Benary ReactionE. Benary, Ber. 63, 1573 (1930); 64, 2543 (1931)Cuvigny, Normant, Bull. Soc. Chim. France 1960, 515.Jutz, Ber. 9 7 (1958).Mechanism: Pasteur et al., Bull. Soc. Chlm. France 1965, 2328.Benkenser ReductionR. A. Benkenser et al., J. Am. Chem Soc. 74, 5699(1952)R. A. Benkenser et al., J. Am. Chem. Soc. 77, 3230 (1955)R. A. Benkenser et al, Tetrahedron Letters no. 16,1df(1960)E.M. Kaiser, Synthesis, 1972, pp391R. A. Benkenser et al, J. Org. Chem. 48, 2796(1983)Benzidine Rearrangement (Semidine Rearrangement)A. W. Hofmann, Proc. Roy. Soc. London 12, 576 (1863)P. Jacobson, F. Henrich and J. Klein, Ber. 26, 688 (1893)G. W. Wheland, Advanced Organic Chemistry (John Wiley, New York, 1949), p 574R. Robinson, J. Chem. Soc. 1941,220G. S. Hammond and H. J. Shine, J. Am. Chem. Soc., 72, 220 (1950)E. D. Hughes, C. K. Ingold, Quart. Revs. 6, 53,1952)G. Wittig and J. E. Grolig, Ber., 94, 2148 (1961)H. J. Shine and 1. T. Chamness, J. Org. Chem., 28, 1232 (1963).Benzilic Acid Rearrangement.J. Liebig, Ann. 25, 27 (1838)N. Zinin, Ann. 31, 329 (1839)C. W. Porter, Molecular Rearrangements (Chemical Catalog Co., New York, 1928), p 100W. von E. Doering and R. S.Urban, J. Am. Chem. Soc. 78, 5938 (1956)J. Hine and H. W. Haworth,.J. Am. Chem. Soc. 80, 2274 (1958)V. Franzen, Chem. Ztg. 82, 105 (1958)E. S. Gould Mechanism and Structure in Organic Chemistry (Holt, Rinehart and Whiston, New York, 1959), p 635S. Selman and J. F. Eastham, Quart. Rev. (London) 14, 221 (1960)Benzoin Condensation.A. J. Lapworth, J. Chem. Soc. 83, 995(1903); 85, 1206 (1904)H. Staudinger, Ber. 46, 3530, 3535 (1913)W. S. Ide and J. S. Buck, Organic Reactions IV, p 269 (New York, 1948)H. von Euler and B. Eistert, Chemie und Biochemie der Reduktone und Reduktonate, p 24(Stuttgart, 1957)L. F. Fieser and M. Fieser, Advanced Organic Chemistry, p 838 (New York, 1961) Also see Acyloin Condensation Bergman ReactionR.R. Jones, R.G. Bergman, J.Am. Chem. Soc, 94, 660(1972)R.G. Bergman, Accts. Chem. Res. 6. 25(1973)J. W. Grissom et al, Tetrahedron 50, 4635(1994)E. Kraka, D. Cremer, J. Am. Chem. Soc. 116,4929(1994)K. C. Nicolaou et al., Proc. Nat. Acad. Sci. USA 90, 5881-(1993)K. Nicolaou, Chem. Birt. 41,33-(1994)Bergmann Azlactone Peptide Synthesis.M. Bergmann, F. Stern and C. Witte, Ann. 449, 277 (1926)J. S. Fruton, Advances In Protein Chemistry V, p 15 (New York, 1949)D. M. Greenberg, Amino Acids and Proteins, p 181 (Springfield, Ill., 1951)H. D. Springall, The Structural Chemistry of Proteins, p 29 (New York, 1954)E. Baltazzi, Quart. Revs. (London) 10, 235 (1956) Also see Erlenmeyer-Plochl Azlactone and Amino Acid Synthesis Bergmann Degradation.M. Bergmann, Science 79, 439 (1934)M. Bergmann and L. Zervas, J. Biol. Chem. 113, 341 (1936)F. C. Whitmore, Organic Chemistry, p 514 (New York, 1951)H. D. Springall, The Structural Chemistry of Proteins, p 321 (New York, 1954) Also see Curtius Rearrangement (Curtious Reaction) Bergmaml-Zervas Carbobenzoxy Method. M. Bergmann and L. Zervas, Ber. 65, 1192 (1932)C. l., A. Schmidt, The Chemistry of the Amino Acids and Proteins, p 262 (Springfield, Ill., 1944)D. M. Greenberg, Amino Acids and Proteins, p 177 (Springfield, Ill., 1951)G. W. Kenner, J. Chem. Soc. 1956, 3689L. F. Fieser and M. Fieser, Advanced Organic Chemistry, p 1040 (New York, 1961) Also see Fischer Peptide Synthesis Bernthsen Acridine SynthesisA. Bernthsen, Ann. 192, 1 (1878); 224, 1 (1884)A. Albert, The Acridines, p 67 (London, 1951)Elderfield, Hetetocyclic Compound et at., J. Chem. Soc. 1955, 1082F. D. Popp, J. Org. Chem. 27, 2658 (1962)Betti Reaction.M. Betti, Gazz. Chim. Ital. 30 II, 301 (l900); 33 II, 2 (l903)F. Pirrone, ibid. 66, 518 (1936); 67, 529 (1937)Phillips, Chem. Revs. 56, 286 (1956)Phillips et al., J. Am. Chem. Soc. 75, 4306 (1953); 77, 5504 (1955)Phillips, Barrall,J