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Volumn 105, Issue 4, 1983, Pages 933-943

Intramolecular Cycloaddition Reactions of Diazoalkenes. A Theoretical Prognosis of Nitrene Type Behavior

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EID: 0037606916     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00342a049     Document Type: Article
Times cited : (36)

References (75)
  • 2
    • 0004250303 scopus 로고
    • The Chemistry of Alkenes
    • Patai, S., Ed.; Interscience: London
    • Huisgen, R.; Grashey, R.; Sauer, J. “The Chemistry of Alkenes”; Patai, S., Ed.; Interscience: London, 1964; pp. 806-878.
    • (1964) , pp. 806-878
    • Huisgen, R.1    Grashey, R.2    Sauer, J.3
  • 10
    • 85022263249 scopus 로고
    • Bull Chem. Soc. Jpn. 1973, 46, 2571.
    • Kondo, K.; Ojima, I. Chem. Lett. 1972, 771; Bull Chem. Soc. Jpn. 1973, 46, 2571.
    • (1972) Chem. Lett. , pp. 771
    • Kondo, K.1    Ojima, I.2
  • 29
    • 85012418847 scopus 로고
    • 1977, 99, 1514. Padwa, A.; Ku, A.; Mazzu, A.; Wetmore, S.I.J. Am. Chem. Soc. 1976, 98, 1048. Padwa, A.; Carlsen, P.H.J.; Ku, A.J. Am. Chem. Soc. 1977, 99, 2798. Padwa, A.; Kamigata, N.J. Am. Chem. Soc. 1977, 99, 1871.
    • Padwa, A.; Carlsen, P.H.J. J. Am. Chem. Soc. 1975, 97, 3682; 1977, 99, 1514. Padwa, A.; Ku, A.; Mazzu, A.; Wetmore, S.I.J. Am. Chem. Soc. 1976, 98, 1048. Padwa, A.; Carlsen, P.H.J.; Ku, A.J. Am. Chem. Soc. 1977, 99, 2798. Padwa, A.; Kamigata, N.J. Am. Chem. Soc. 1977, 99, 1871.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 3682
    • Padwa, A.1    Carlsen, P.H.J.2
  • 32
    • 0008580515 scopus 로고
    • Garantí, L.; Zecchi, G.J. Chem. Soc, Perkin Trans 1 1977, 2092.
    • Garantí, L.; Vigevami, A.; Zecchi, G. Tetrahedron Lett. 1976, 1527. Garantí, L.; Zecchi, G.J. Chem. Soc, Perkin Trans 1 1977, 2092.
    • (1976) Tetrahedron Lett. , pp. 1527
    • Garantí, L.1    Vigevami, A.2    Zecchi, G.3
  • 35
    • 33847086094 scopus 로고
    • Miyashi, T.; Fujii, Y.; Nishizawa, Y.; Mukai, T.J. Am. Chem. Soc. 1981, 103, 725.
    • Nishizawa, Y.; Miyashi, T.; Mukai, T. J. Am. Chem. Soc. 1980, 102, 1176. Miyashi, T.; Fujii, Y.; Nishizawa, Y.; Mukai, T.J. Am. Chem. Soc. 1981, 103, 725.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 1176
    • Nishizawa, Y.1    Miyashi, T.2    Mukai, T.3
  • 41
    • 33947336656 scopus 로고
    • Org. Synth. 1970, 50, 72.
    • Corey, E.J.; Seebach, D. J. Org. Chem. 1966, 31, 4097; Org. Synth. 1970, 50, 72.
    • (1966) J. Org. Chem. , vol.31 , pp. 4097
    • Corey, E.J.1    Seebach, D.2
  • 43
    • 0004289338 scopus 로고
    • Nitrenes
    • Interscience: New York
    • Lwowski, W. “Nitrenes”, Interscience: New York, 1970.
    • (1970)
    • Lwowski, W.1
  • 44
    • 0004271089 scopus 로고
    • The Chemistry of Diazonium and Diazo Groups
    • Intermolecular 1, 1 cycloaddition is suggested in the reaction of 2-diazo-4, 5-dicyanoimidazole with electron-rich olefins, e.g., 1, 2-dimethoxy-ethylene. (a), Patai, S., Ed.; Wiley-Interscience: New York, (b) Sheppard, W.A.; Webster, O.W.J. Am. Chem. Soc. 1973, 95, 2695.
    • Intermolecular 1, 1 cycloaddition is suggested in the reaction of 2-diazo-4, 5-dicyanoimidazole with electron-rich olefins, e.g., 1, 2-dimethoxy-ethylene. (a) Wulfman, D.S.; Linstrumelle, G.; Copper, C.F. “The Chemistry of Diazonium and Diazo Groups”; Patai, S., Ed.; Wiley-Interscience: New York, 1978; p. 905. (b) Sheppard, W.A.; Webster, O.W.J. Am. Chem. Soc. 1973, 95, 2695.
    • (1978) , pp. 905
    • Wulfman, D.S.1    Linstrumelle, G.2    Copper, C.F.3
  • 45
    • 0042403925 scopus 로고
    • Lemal, D.M.; Shim, K.S. Tetrahedron Lett. 1964, 3231. Schneider, M.; Csacsko, B. Angew Chem., Int. Ed. Engl. 1977, 16, 867.
    • Lemal, D.M.; Menger, F.; Clark, G.W. J. Am. Chem. Soc. 1963, 85, 2529. Lemal, D.M.; Shim, K.S. Tetrahedron Lett. 1964, 3231. Schneider, M.; Csacsko, B. Angew Chem., Int. Ed. Engl. 1977, 16, 867.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2529
    • Lemal, D.M.1    Menger, F.2    Clark, G.W.3
  • 46
    • 33947091542 scopus 로고
    • Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew Chem., Int. Ed. Engl. 1979, 18, 729.
    • Atkins, R.C.; Trost, B.M. J. Org. Chem. 1972, 37, 3133. Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew Chem., Int. Ed. Engl. 1979, 18, 729.
    • (1972) J. Org. Chem. , vol.37 , pp. 3133
    • Atkins, R.C.1    Trost, B.M.2
  • 47
    • 49849122366 scopus 로고
    • Scholkopf, U.; Rieber, N. Chem. Ber. 1969, 102, 488. Hartmann, A.; Welter, W.; Regitz, M. Tetrahedron Lett. 1974, 1825. Heydt, H.; Busch, K.-H.; Regitz, M. Liebigs Ann. Chem. 1980, 590.
    • Franck-Neumann, M.; Buchecker, C. Tetrahedron Lett. 1969, 2659. Scholkopf, U.; Rieber, N. Chem. Ber. 1969, 102, 488. Hartmann, A.; Welter, W.; Regitz, M. Tetrahedron Lett. 1974, 1825. Heydt, H.; Busch, K.-H.; Regitz, M. Liebigs Ann. Chem. 1980, 590.
    • (1969) Tetrahedron Lett. , pp. 2659
    • Franck-Neumann, M.1    Buchecker, C.2
  • 48
    • 0000141448 scopus 로고
    • Hariharan, P.C.; Pople, J.A. Chem. Phys. Lett. 1972, 16, 217.
    • Ditchfield, R.; Hehre, W.J.; Pople, J.A. J. Chem. Phys. 1971, 54, 724. Hariharan, P.C.; Pople, J.A. Chem. Phys. Lett. 1972, 16, 217.
    • (1971) J. Chem. Phys. , vol.54 , pp. 724
    • Ditchfield, R.1    Hehre, W.J.2    Pople, J.A.3
  • 49
    • 85023405292 scopus 로고    scopus 로고
    • NRCC Program QG01
    • We thank Dr. J.J. Wendoloski for running calculations reported.
    • (a) Du Puis, M.; Spangler, D.; Wendoloski, J.J. NRCC Program QG01. We thank Dr. J.J. Wendoloski for running calculations reported
    • Du Puis, M.1    Spangler, D.2    Wendoloski, J.J.3
  • 51
    • 0004271089 scopus 로고
    • The Chemistry of Diazonium and Diazo Groups
    • Patai, S., Ed.; Wiley-Interscience: New York, (b) Houk, K.N.; Sims, J.; Duke, R.E., Jr.; Strozier, R.W.; George, J.K.J. Am. Chem. Soc. 1973, 95, 7287 and references therein, (c) Leroy, G.; Sana, M. Theor. Chim. Acta 1974, 33, 329.
    • (a) Sorriso, S. “The Chemistry of Diazonium and Diazo Groups”; Patai, S., Ed.; Wiley-Interscience: New York, 1978; p. 95. (b) Houk, K.N.; Sims, J.; Duke, R.E., Jr.; Strozier, R.W.; George, J.K.J. Am. Chem. Soc. 1973, 95, 7287 and references therein, (c) Leroy, G.; Sana, M. Theor. Chim. Acta 1974, 33, 329.
    • (1978) , pp. 95
    • Sorriso, S.1
  • 52
    • 0343612026 scopus 로고
    • Huisgen, R.; Geittner, J. Heterocycles 1978, 11, 105. (c) Bihlmaier, W.; Huisgen, R.; Reissig, H.-U.; Voss, S. Tetrahedron Lett. 1979, 2621.
    • (a) Geittner, J.; Huisgen, R.; Reissig, H.-U. Heterocycles 1978, 11, 109. (b) Huisgen, R.; Geittner, J. Heterocycles 1978, 11, 105. (c) Bihlmaier, W.; Huisgen, R.; Reissig, H.-U.; Voss, S. Tetrahedron Lett. 1979, 2621.
    • (1978) Heterocycles , vol.11 , pp. 109
    • Geittner, J.1    Huisgen, R.2    Reissig, H.-U.3
  • 54
    • 2342653797 scopus 로고
    • Molecular Spectra and Molecular Structure III. Electronic Spectra and Electronic Structure of Polyatomic Molecules
    • Van Nostrand: Toronto, Canada
    • Herzberg, G. “Molecular Spectra and Molecular Structure III. Electronic Spectra and Electronic Structure of Polyatomic Molecules”; Van Nostrand: Toronto, Canada, 1967.
    • (1967)
    • Herzberg, G.1
  • 55
    • 84977258365 scopus 로고
    • Wittig, G.; Haag, W. Chem. Ber. 1955, 88, 1654.
    • Staudinger, H.; Meyer, J. Heiv. Chim. Acta 1919, 2, 619. Wittig, G.; Haag, W. Chem. Ber. 1955, 88, 1654.
    • (1919) Heiv. Chim. Acta , vol.2 , pp. 619
    • Staudinger, H.1    Meyer, J.2
  • 57
    • 0004271089 scopus 로고
    • The Chemistry of Diazonium and Diazo Groups
    • Patai, S., Ed.; Wiley-Interscience: New York
    • McGarriety, J.F. “The Chemistry of Diazonium and Diazo Groups”; Patai, S., Ed.; Wiley-Interscience: New York, 1978; p. 179.
    • (1978) , pp. 179
    • McGarriety, J.F.1
  • 58
    • 85023419259 scopus 로고    scopus 로고
    • The deformation of 10° and 20° require 1.6 and 5.6 kcal, respectively, by CNDO/2
    • The deformation of 10° and 20° require 1.6 and 5.6 kcal, respectively, by CNDO/2.
  • 59
    • 85023332374 scopus 로고    scopus 로고
    • The styryl group in 10 is most likely nonplanar60 and not as nucleophilic as the E stereoisomer 2
    • The styryl group in 10 is most likely nonplanar60 and not as nucleophilic as the E stereoisomer 2.
  • 61
    • 0040458535 scopus 로고
    • Hoffmann, R.J. Am. Chem. Soc. 1968, 90, 1475.
    • Hoffmann, R.; Hayes, D.M.; Skell, P.S. J. Phys. Chem. 1972, 76, 664. Hoffmann, R.J. Am. Chem. Soc. 1968, 90, 1475.
    • (1972) J. Phys. Chem. , vol.76 , pp. 664
    • Hoffmann, R.1    Hayes, D.M.2    Skell, P.S.3
  • 62
    • 84985553196 scopus 로고
    • Huisgen, R.; Bihlmaier, W.; Reissig, H.-U. Angew. Chem., Int. Ed. Engl. 1979, 18, 331. (c) Bihlmaier, W.; Huisgen, R.; Reissig, H.-U.; Voss, S. Tetrahedron Lett. 1979, 2621. (d) Huisgen, R.; Reissign, H.-U.; Huber, H.; Voss, S. Tetrahedron Lett. 1979, 2987.
    • (a) Huisgen, R.; Reissig, H.-U. Angew. Chem., Int. Ed. Engl. 1979, 18, 330. (b) Huisgen, R.; Bihlmaier, W.; Reissig, H.-U. Angew. Chem., Int. Ed. Engl. 1979, 18, 331. (c) Bihlmaier, W.; Huisgen, R.; Reissig, H.-U.; Voss, S. Tetrahedron Lett. 1979, 2621. (d) Huisgen, R.; Reissign, H.-U.; Huber, H.; Voss, S. Tetrahedron Lett. 1979, 2987.
    • (1979) Angew. Chem., Int. Ed. Engl. , vol.18 , pp. 330
    • Huisgen, R.1    Reissig, H.-U.2


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