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PhCH=P(MeNCH2CH2)3N: A Novel Ylide for Quantitative E Selectivity in the Wittig Reaction

Zhigang Wang, Guangtao Zhang, Ilia Guzei and John G. Verkade*

*Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, Email: jverkadeiastate.edu

Z. Wang, G. Zhang, I. Guzei, J. G. Verkade, J. Org. Chem., 2001, 66, 3521-3524.

DOI: 10.1021/jo0100704 (free Supporting Information)


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Abstract

The semi-stabilized ylide PhCH=P(MeNCH2CH2)3N, which is readily prepared from the commercially available base P(MeNCH2CH2)3N, reacts with aldehydes to give alkenes in high yield with quantitative E selectivity. The E selectivity is discussed.


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proposed intermediates



Key Words

Wittig Reaction


ID: J42-Y2001-130