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Volumn 8, Issue 6, 1997, Pages 557-569

Theoretical study of the mechanism of the wittig reaction: Ab initio and MNDO-PM3 treatment of the reaction of unstabilized, semistabilized and stabilized ylides with acetaldehyde

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EID: 0038159938     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1071(1997)8:6<557::AID-HC16>3.0.CO;2-Q     Document Type: Article
Times cited : (28)

References (37)
  • 1
    • 85033296164 scopus 로고    scopus 로고
    • Molecular modeling of the Wittig reaction 6
    • (a) Molecular modeling of the Wittig reaction 6;
  • 3
    • 6444221894 scopus 로고    scopus 로고
    • For recent reviews of the Wittig reaction, see (a) B. J. Walker, Organophosphorus Chem. 27, 1996, 264; (b) A. W. Johnson, Ylides and Imines of Phosphorus, Wiley, New York, (1993); B. Maryanoff, A. E. Reitz, Chem. Rev., 89, 1989, 863.
    • (1996) Organophosphorus Chem. , vol.27 , pp. 264
    • Walker, B.J.1
  • 4
    • 0003397099 scopus 로고
    • Wiley, New York
    • For recent reviews of the Wittig reaction, see (a) B. J. Walker, Organophosphorus Chem. 27, 1996, 264; (b) A. W. Johnson, Ylides and Imines of Phosphorus, Wiley, New York, (1993); B. Maryanoff, A. E. Reitz, Chem. Rev., 89, 1989, 863.
    • (1993) Ylides and Imines of Phosphorus
    • Johnson, A.W.1
  • 5
    • 0001848341 scopus 로고
    • For recent reviews of the Wittig reaction, see (a) B. J. Walker, Organophosphorus Chem. 27, 1996, 264; (b) A. W. Johnson, Ylides and Imines of Phosphorus, Wiley, New York, (1993); (c) B. Maryanoff, A. E. Reitz, Chem. Rev., 89, 1989, 863.
    • (1989) Chem. Rev. , vol.89 , pp. 863
    • Maryanoff, B.1    Reitz, A.E.2
  • 6
    • 0002827445 scopus 로고
    • For recent reviews of the Mechanism and Stereoselectivity of the Wittig reaction, see (a) E. Vedejs, M. J. Peterson, Top. Stereochem. 21, 1994, 1; (b) E. Vedejs, M. J. Peterson, Adv. Carbanion Chem. 2, 1994, 1.
    • (1994) Top. Stereochem. , vol.21 , pp. 1
    • Vedejs, E.1    Peterson, M.J.2
  • 7
    • 0004008588 scopus 로고
    • For recent reviews of the Mechanism and Stereoselectivity of the Wittig reaction, see (a) E. Vedejs, M. J. Peterson, Top. Stereochem. 21, 1994, 1; (b) E. Vedejs, M. J. Peterson, Adv. Carbanion Chem. 2, 1994, 1.
    • (1994) Adv. Carbanion Chem. , vol.2 , pp. 1
    • Vedejs, E.1    Peterson, M.J.2
  • 11
    • 85033299944 scopus 로고    scopus 로고
    • note
    • The observation of unusually stable oxaphosphetanes derived from one semistabilized[5] and one stabilized ylide[8] has recently been reported. In the semistabilized case, a dibenzophosphole substituted phosphorus atom in the oxaphosphetane is stabilized relative to the phosphine oxide product, hence the decomposition rate is retarded. In the stabilized case, resistance to oxaphosphetane decomposition is provided by the stabilizing effects of electron-withdrawing groups and ring strain on the phosphorus atom.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.