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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 6
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Original Articles

Betaine Decomposition Studies of Arsonium Ylides Leading to Lactonyl and Lactothionyl Olefination

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Pages 457-464 | Published online: 05 Dec 2006
 

Abstract

The synthetic potential of the Wittig reaction has reached the maximum as a most versatile tool for carbonyl olefination1–4, but our interest in this field arises from a wish to extend this area to some other types of olefination reactions.5,6 Until now it has been well established that olefination, either via phosphonium ylides or arsonium ylides, proceeds via stepwise formation of a betaine type compound and a four membered intermediate. It is the decomposition pattern of the betaines which is mainly responsible for the nature of product formation. We have recently carried out a thorough investigation of the arsonium betaines of carbonyls and exocyclic thiocarbonyls.7,8 However, the decomposition pattern of betaines formed by the nucleophilic attack of these ylides on α-lactonyl and α-lactothionyl systems still remains uninvestigated.

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