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Introduction to the Wittig Reaction and Discussion of the Mechanism

  • Peter A. Byrne
Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

The Wittig reaction [1] is perhaps the most commonly used method for the synthesis of alkenes. Several excellent reviews on the topic have previously been written [2–5]. The reaction (see Scheme 1.1) occurs between a carbonyl compound (aldehyde or ketone in general, 2) and a phosphonium ylide (1). The latter species is a carbanion stabilised by an adjacent phosphorus substituted with three carbons, giving alkene (3) and phosphine oxide (4) as the by-product. The ylide can be represented by resonance structures 1a (fully ionic ylide form) and 1b (ylene form), which show between them the ionic character of the P–C bond and the contribution to the stabilisation of the carbanion by phosphorus.

Keywords

Phosphine Oxide Steric Interaction Kinetic Control Phosphonium Salt Wittig Reaction 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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© Springer-Verlag Berlin Heidelberg 2012

Authors and Affiliations

  1. 1.School of Chemistry and Chemical BiologyUniversity College DublinDublinIreland

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