Tetrahedron

An easy access to trisubstituted vinyl chlorides and improved synthesis of chloro/bromostilbenes

C Muthiah, KP Kumar, S Kumaraswamy, KCK Swamy

Index: Muthiah; Kumar, K. Praveen; Kumaraswamy, Sudha; Kumara Swamy Tetrahedron, 1998 , vol. 54, # 47 p. 14315 - 14326

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Citation Number: 18

Abstract

The α-chlorophosphonates (OCH2CMe2CH2O) P (O) CHCl-C6H4-4-R [R= H (4), Me (5), OMe (6)], which are now readily accessible, react with ketones R′ C (O) R ″in the presence of NaH (without recourse to the more expensive t-BuLi) to afford trisubstituted vinyl halides R′ C (R ″)= CCl (C6H4-4-R) in good yields. The corresponding α- bromophosphonates [R= H (7), Me (8)] failed to react with ketones and gave the ...