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Original Articles

Convenient Synthesis of 1-(Trimethylsilyl)- and 1-(Trimethylstannyl)Vinylphosphonates and Their Synthetic Application

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Pages 922-924 | Received 29 Aug 2014, Accepted 15 Oct 2014, Published online: 01 Jul 2015
 

GRAPHICAL ABSTRACT

Abstract

Dimethyl 1,1-bis(trimethylsilyl)methylphosphonate was succeeded to react with aromatic aldehydes in the presence of methyl benzoate as additive to give the corresponding vinylphosphonates in moderate yields. Michael addition and subsequent Peterson olefination reaction of dimethyl (Z)-2-(3,4-methylenedioxyphenyl)-1-(trimethylsilyl)vinylphosphonate with 3,4,5-trimethoxyphenyllithium and crotonaldehyde afforded the corresponding (2E,4E)-1-(3,4,5-trimethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-2-(dimethylphosphono)hexa-2,4-diene in 36% yield.

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