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Volumn 15, Issue 21, 1996, Pages 4612-4617

Synthesis of 2-acylvinyl ethers by reaction of chromium (fischer) carbene complexes and stabilized sulfur ylides

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EID: 0000390623     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960441k     Document Type: Article
Times cited : (17)

References (35)
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    • For reviews on the chemistry of group 6 metal carbene complexes, see, for example: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5. (b) Transition Metal Carbene Complexes; Verlag Chemie: Weinheim, Germany, 1983. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587.
    • (1990) Comprehensive Organic Synthesis , vol.5
    • Wulff, W.D.1
  • 5
    • 0003818422 scopus 로고
    • Verlag Chemie: Weinheim, Germany
    • For reviews on the chemistry of group 6 metal carbene complexes, see, for example: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5. (b) Transition Metal Carbene Complexes; Verlag Chemie: Weinheim, Germany, 1983. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587.
    • (1983) Transition Metal Carbene Complexes
  • 6
    • 84985559908 scopus 로고
    • For reviews on the chemistry of group 6 metal carbene complexes, see, for example: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5. (b) Transition Metal Carbene Complexes; Verlag Chemie: Weinheim, Germany, 1983. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 587
    • Dötz, K.H.1
  • 8
    • 17444403825 scopus 로고
    • For a review on the Wittig olefination with carbonyl compounds other than aldehydes and ketones, see: Murphy, P. J.; Brennan, J. Chem. Soc. Rev. 1988, 17, 1.
    • (1988) Chem. Soc. Rev. , vol.17 , pp. 1
    • Murphy, P.J.1    Brennan, J.2
  • 19
    • 33947485009 scopus 로고
    • The following nonstabilized ylides were tested: Dimethylsulfonium methylide, diphenylsulfonium cyclopropylide, tetrahydrothiophenylethylide, and tetrahydrothiophenylbenzylide. (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (b) Trost, B. M.; Bogdanowicz, M. J. Am. Chem. Soc. 1971, 93, 3773. Phase-transfer modification (c) Borredon, M. E.; Delmas, M.; Gaset, A. Tetrahedron 1987, 43, 3945.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 1353
    • Corey, E.J.1    Chaykovsky, M.2
  • 20
    • 0007642114 scopus 로고
    • Phase-transfer modification
    • The following nonstabilized ylides were tested: Dimethylsulfonium methylide, diphenylsulfonium cyclopropylide, tetrahydrothiophenylethylide, and tetrahydrothiophenylbenzylide. (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (b) Trost, B. M.; Bogdanowicz, M. J. Am. Chem. Soc. 1971, 93, 3773. Phase-transfer modification (c) Borredon, M. E.; Delmas, M.; Gaset, A. Tetrahedron 1987, 43, 3945.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 3773
    • Trost, B.M.1    Bogdanowicz, M.2
  • 21
    • 45949130191 scopus 로고
    • The following nonstabilized ylides were tested: Dimethylsulfonium methylide, diphenylsulfonium cyclopropylide, tetrahydrothiophenylethylide, and tetrahydrothiophenylbenzylide. (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353. (b) Trost, B. M.; Bogdanowicz, M. J. Am. Chem. Soc. 1971, 93, 3773. Phase-transfer modification (c) Borredon, M. E.; Delmas, M.; Gaset, A. Tetrahedron 1987, 43, 3945.
    • (1987) Tetrahedron , vol.43 , pp. 3945
    • Borredon, M.E.1    Delmas, M.2    Gaset, A.3
  • 22
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    • 3 at room temperature for a few days a similar change in the E/Z composition of some samples has been observed
    • 3 at room temperature for a few days a similar change in the E/Z composition of some samples has been observed.
  • 26
    • 0000796418 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York
    • For a review on the synthesis of enol ethers, see: Chan, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, pp 595-628.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 595-628
    • Chan, T.H.1
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    • Direct sun-light is preferred due to considerably shorter oxidation times
    • Direct sun-light is preferred due to considerably shorter oxidation times.


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