Theoretical study on the substituent effect of a Wittig reaction

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

Detail(s)

Original languageEnglish
Pages (from-to)206-210
Journal / PublicationTheoretical Chemistry Accounts
Volume107
Issue number4
Publication statusPublished - 2002

Abstract

The substituent effects of F, H and methyl (Me) in replacement of phenyl (Ph) groups bonding with the ylide phosphorus in Wittig reactions have been examined theoretically by performing ab intio calculations. It is shown that the energy barrier for the Wittig reaction with F as the substituent is much higher than that with H, Me and Ph. The Wittig reaction is found to be more favorable with the substituent in the order F <H <Ph <Me. The reactions are found to proceed through two transition states: the formation and the decomposition of oxaphosphetane. We conclude that only the model of the Wittig reaction in which Ph is simplified to Me can reasonably describe the real Wittig reaction. © Springer-Verlag 2002.

Research Area(s)

  • Substituent effect, Wittig reaction

Citation Format(s)

Theoretical study on the substituent effect of a Wittig reaction. / Lu, W. C.; Wong, N. B.; Zhang, R. Q.
In: Theoretical Chemistry Accounts, Vol. 107, No. 4, 2002, p. 206-210.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review