메뉴 건너뛰기




Volumn 77, Issue 5-6, 1999, Pages 760-773

General acid-catalyzed addition of methanol to (E)-N-benzylideneanilines

Author keywords

Free energy linear relationship; Imine; More O'Ferrall Jencks diagram; Nucleophilic addition; Schiff base

Indexed keywords

ANILINE DERIVATIVE; CARBOXYLIC ACID; METHANOL; SCHIFF BASE;

EID: 0033306103     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v99-070     Document Type: Article
Times cited : (4)

References (86)
  • 2
    • 6244286142 scopus 로고
    • M. Brezina and P. Zuman. Chem. Listy, 47, 975 (1953); J. Hine and C.Y. Yeh. J. Am. Chem. Soc. 89, 2669 (1967); J. Hine, C. Y. Yeh, and F.C. Schmalstieg. J. Org. Chem. 35, 340 (1970); A. Williams and M.L. Bender. J. Am. Chem. Soc. 88. 2508 (1966); B.M. Anderson and W.P. Jencks. J. Am. Chem. Soc. 82, 1773 (1960); R. Rosenberg, S.M. Silver, J.M. Sayer, and W.P. Jencks. J. Am. Chem. Soc. 96, 7986 (1974); J.M. Sayer and C. Edman. J. Am. Chem. Soc. 101, 3010 (1979); J. Hine, J.P. Ziegler, and M. Johnston. J. Org. Chem. 44, 3540 (1979).
    • (1953) Chem. Listy , vol.47 , pp. 975
    • Brezina, M.1    Zuman, P.2
  • 3
    • 33947335911 scopus 로고
    • M. Brezina and P. Zuman. Chem. Listy, 47, 975 (1953); J. Hine and C.Y. Yeh. J. Am. Chem. Soc. 89, 2669 (1967); J. Hine, C. Y. Yeh, and F.C. Schmalstieg. J. Org. Chem. 35, 340 (1970); A. Williams and M.L. Bender. J. Am. Chem. Soc. 88. 2508 (1966); B.M. Anderson and W.P. Jencks. J. Am. Chem. Soc. 82, 1773 (1960); R. Rosenberg, S.M. Silver, J.M. Sayer, and W.P. Jencks. J. Am. Chem. Soc. 96, 7986 (1974); J.M. Sayer and C. Edman. J. Am. Chem. Soc. 101, 3010 (1979); J. Hine, J.P. Ziegler, and M. Johnston. J. Org. Chem. 44, 3540 (1979).
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 2669
    • Hine, J.1    Yeh, C.Y.2
  • 4
    • 0001364392 scopus 로고
    • M. Brezina and P. Zuman. Chem. Listy, 47, 975 (1953); J. Hine and C.Y. Yeh. J. Am. Chem. Soc. 89, 2669 (1967); J. Hine, C. Y. Yeh, and F.C. Schmalstieg. J. Org. Chem. 35, 340 (1970); A. Williams and M.L. Bender. J. Am. Chem. Soc. 88. 2508 (1966); B.M. Anderson and W.P. Jencks. J. Am. Chem. Soc. 82, 1773 (1960); R. Rosenberg, S.M. Silver, J.M. Sayer, and W.P. Jencks. J. Am. Chem. Soc. 96, 7986 (1974); J.M. Sayer and C. Edman. J. Am. Chem. Soc. 101, 3010 (1979); J. Hine, J.P. Ziegler, and M. Johnston. J. Org. Chem. 44, 3540 (1979).
    • (1970) J. Org. Chem. , vol.35 , pp. 340
    • Hine, J.1    Yeh, C.Y.2    Schmalstieg, F.C.3
  • 5
    • 0010112913 scopus 로고
    • M. Brezina and P. Zuman. Chem. Listy, 47, 975 (1953); J. Hine and C.Y. Yeh. J. Am. Chem. Soc. 89, 2669 (1967); J. Hine, C. Y. Yeh, and F.C. Schmalstieg. J. Org. Chem. 35, 340 (1970); A. Williams and M.L. Bender. J. Am. Chem. Soc. 88. 2508 (1966); B.M. Anderson and W.P. Jencks. J. Am. Chem. Soc. 82, 1773 (1960); R. Rosenberg, S.M. Silver, J.M. Sayer, and W.P. Jencks. J. Am. Chem. Soc. 96, 7986 (1974); J.M. Sayer and C. Edman. J. Am. Chem. Soc. 101, 3010 (1979); J. Hine, J.P. Ziegler, and M. Johnston. J. Org. Chem. 44, 3540 (1979).
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2508
    • Williams, A.1    Bender, M.L.2
  • 6
    • 0001740905 scopus 로고
    • M. Brezina and P. Zuman. Chem. Listy, 47, 975 (1953); J. Hine and C.Y. Yeh. J. Am. Chem. Soc. 89, 2669 (1967); J. Hine, C. Y. Yeh, and F.C. Schmalstieg. J. Org. Chem. 35, 340 (1970); A. Williams and M.L. Bender. J. Am. Chem. Soc. 88. 2508 (1966); B.M. Anderson and W.P. Jencks. J. Am. Chem. Soc. 82, 1773 (1960); R. Rosenberg, S.M. Silver, J.M. Sayer, and W.P. Jencks. J. Am. Chem. Soc. 96, 7986 (1974); J.M. Sayer and C. Edman. J. Am. Chem. Soc. 101, 3010 (1979); J. Hine, J.P. Ziegler, and M. Johnston. J. Org. Chem. 44, 3540 (1979).
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 1773
    • Anderson, B.M.1    Jencks, W.P.2
  • 7
    • 0000134367 scopus 로고
    • M. Brezina and P. Zuman. Chem. Listy, 47, 975 (1953); J. Hine and C.Y. Yeh. J. Am. Chem. Soc. 89, 2669 (1967); J. Hine, C. Y. Yeh, and F.C. Schmalstieg. J. Org. Chem. 35, 340 (1970); A. Williams and M.L. Bender. J. Am. Chem. Soc. 88. 2508 (1966); B.M. Anderson and W.P. Jencks. J. Am. Chem. Soc. 82, 1773 (1960); R. Rosenberg, S.M. Silver, J.M. Sayer, and W.P. Jencks. J. Am. Chem. Soc. 96, 7986 (1974); J.M. Sayer and C. Edman. J. Am. Chem. Soc. 101, 3010 (1979); J. Hine, J.P. Ziegler, and M. Johnston. J. Org. Chem. 44, 3540 (1979).
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 7986
    • Rosenberg, R.1    Silver, S.M.2    Sayer, J.M.3    Jencks, W.P.4
  • 8
    • 0018466475 scopus 로고
    • M. Brezina and P. Zuman. Chem. Listy, 47, 975 (1953); J. Hine and C.Y. Yeh. J. Am. Chem. Soc. 89, 2669 (1967); J. Hine, C. Y. Yeh, and F.C. Schmalstieg. J. Org. Chem. 35, 340 (1970); A. Williams and M.L. Bender. J. Am. Chem. Soc. 88. 2508 (1966); B.M. Anderson and W.P. Jencks. J. Am. Chem. Soc. 82, 1773 (1960); R. Rosenberg, S.M. Silver, J.M. Sayer, and W.P. Jencks. J. Am. Chem. Soc. 96, 7986 (1974); J.M. Sayer and C. Edman. J. Am. Chem. Soc. 101, 3010 (1979); J. Hine, J.P. Ziegler, and M. Johnston. J. Org. Chem. 44, 3540 (1979).
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 3010
    • Sayer, J.M.1    Edman, C.2
  • 9
    • 6244300326 scopus 로고
    • M. Brezina and P. Zuman. Chem. Listy, 47, 975 (1953); J. Hine and C.Y. Yeh. J. Am. Chem. Soc. 89, 2669 (1967); J. Hine, C. Y. Yeh, and F.C. Schmalstieg. J. Org. Chem. 35, 340 (1970); A. Williams and M.L. Bender. J. Am. Chem. Soc. 88. 2508 (1966); B.M. Anderson and W.P. Jencks. J. Am. Chem. Soc. 82, 1773 (1960); R. Rosenberg, S.M. Silver, J.M. Sayer, and W.P. Jencks. J. Am. Chem. Soc. 96, 7986 (1974); J.M. Sayer and C. Edman. J. Am. Chem. Soc. 101, 3010 (1979); J. Hine, J.P. Ziegler, and M. Johnston. J. Org. Chem. 44, 3540 (1979).
    • (1979) J. Org. Chem. , vol.44 , pp. 3540
    • Hine, J.1    Ziegler, J.P.2    Johnston, M.3
  • 10
    • 0001002375 scopus 로고
    • E.H. Cordes and W.P. Jencks. J. Am. Chem. Soc. 85, 2843 (1963); R.H. Kayser and R.M. Pollack. J. Am. Chem. Soc. 99, 3379 (1977); T. Okuyama, H. Shibuya, and T. Fueno. J. Am. Chem. Soc. 104, 730 (1982).
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2843
    • Cordes, E.H.1    Jencks, W.P.2
  • 11
    • 33847089845 scopus 로고
    • E.H. Cordes and W.P. Jencks. J. Am. Chem. Soc. 85, 2843 (1963); R.H. Kayser and R.M. Pollack. J. Am. Chem. Soc. 99, 3379 (1977); T. Okuyama, H. Shibuya, and T. Fueno. J. Am. Chem. Soc. 104, 730 (1982).
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 3379
    • Kayser, R.H.1    Pollack, R.M.2
  • 12
    • 0020089661 scopus 로고
    • E.H. Cordes and W.P. Jencks. J. Am. Chem. Soc. 85, 2843 (1963); R.H. Kayser and R.M. Pollack. J. Am. Chem. Soc. 99, 3379 (1977); T. Okuyama, H. Shibuya, and T. Fueno. J. Am. Chem. Soc. 104, 730 (1982).
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 730
    • Okuyama, T.1    Shibuya, H.2    Fueno, T.3
  • 15
    • 0010382060 scopus 로고
    • T.I. Crowell, D.H. O'Brien, and M. Neveu. J. Org. Chem. 29, 2043 (1964); R.L. Reeves. J. Org. Chem. 30, 3129 (1965).
    • (1965) J. Org. Chem. , vol.30 , pp. 3129
    • Reeves, R.L.1
  • 20
    • 10044289888 scopus 로고
    • R.P. Bell and W.C.E. Higginson. Proc. R. Soc. London Ser. A, 197, 141 (1949); R.P. Bell. Adv. Phys. Org. Chem. 4, 1 (1966).
    • (1966) Adv. Phys. Org. Chem. , vol.4 , pp. 1
    • Bell, R.P.1
  • 33
    • 0010896669 scopus 로고
    • (b) J. Am. Chem. Soc. 107, 4710 (1985);
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4710
  • 34
    • 0011310842 scopus 로고
    • (c) J. Am. Chem. Soc. 107, 4715 (1985);
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4715
  • 47
    • 0001256177 scopus 로고
    • (b) J. Am. Chem. Soc. 100, 1228 (1978);
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 1228
  • 49
    • 33845558357 scopus 로고
    • J.E. Dubois, M. El-Alaoui, and J. Toullec. J. Am. Chem. Soc. 103, 5393 (1981); J. Toullec, M. El-Alaoui, and P. Kleffert. J. Org. Chem. 48, 4808 (1983); J. Org. Chem. 50, 4928 (1985); J. Toullec and M. El-Alaoui. J. Org. Chem. 51, 4054 (1986).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 5393
    • Dubois, J.E.1    El-Alaoui, M.2    Toullec, J.3
  • 50
    • 6244230728 scopus 로고
    • J.E. Dubois, M. El-Alaoui, and J. Toullec. J. Am. Chem. Soc. 103, 5393 (1981); J. Toullec, M. El-Alaoui, and P. Kleffert. J. Org. Chem. 48, 4808 (1983); J. Org. Chem. 50, 4928 (1985); J. Toullec and M. El-Alaoui. J. Org. Chem. 51, 4054 (1986).
    • (1983) J. Org. Chem. , vol.48 , pp. 4808
    • Toullec, J.1    El-Alaoui, M.2    Kleffert, P.3
  • 51
    • 0011422996 scopus 로고
    • J.E. Dubois, M. El-Alaoui, and J. Toullec. J. Am. Chem. Soc. 103, 5393 (1981); J. Toullec, M. El-Alaoui, and P. Kleffert. J. Org. Chem. 48, 4808 (1983); J. Org. Chem. 50, 4928 (1985); J. Toullec and M. El-Alaoui. J. Org. Chem. 51, 4054 (1986).
    • (1985) J. Org. Chem. , vol.50 , pp. 4928
  • 52
    • 0010616744 scopus 로고
    • J.E. Dubois, M. El-Alaoui, and J. Toullec. J. Am. Chem. Soc. 103, 5393 (1981); J. Toullec, M. El-Alaoui, and P. Kleffert. J. Org. Chem. 48, 4808 (1983); J. Org. Chem. 50, 4928 (1985); J. Toullec and M. El-Alaoui. J. Org. Chem. 51, 4054 (1986).
    • (1986) J. Org. Chem. , vol.51 , pp. 4054
    • Toullec, J.1    El-Alaoui, M.2
  • 55
    • 84986336665 scopus 로고
    • B.A. Korolev, N.A. Rozanel'skaya, and B.I. Stepanov. Zh. Obshch. Khim. 39, 1161 (1968); J. Genet. Chem. U.S.S.R. 39, 1128 (1969).
    • (1969) J. Genet. Chem. U.S.S.R. , vol.39 , pp. 1128
  • 66
    • 6244222752 scopus 로고
    • (a) S.B. Bulgarevich, S.I. Adamova, A.A. Polunin, V.A. Kogan, and O.A. Osipov. Zh. Obshch. 47, 1144 (1977); J. Genet. Chem. U.S.S.R. 47, 1050 (1977);
    • (1977) J. Genet. Chem. U.S.S.R. , vol.47 , pp. 1050
  • 71
    • 6844222119 scopus 로고
    • (c) N. Russo. THEOCHEM, 41, 403 (1988).
    • (1988) Theochem , vol.41 , pp. 403
    • Russo, N.1
  • 75
    • 3042520570 scopus 로고
    • (c) Chem. Rev. 85, 511 (1985).
    • (1985) Chem. Rev. , vol.85 , pp. 511
  • 76
    • 84901486385 scopus 로고
    • Glossary of terms used in physical organic chemistry (UIPAC recommendations 1994)
    • Glossary of terms used in physical organic chemistry (UIPAC recommendations 1994). Pure Appl. Chem. 66, 1077 (1994).
    • (1994) Pure Appl. Chem. , vol.66 , pp. 1077


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.