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1-acetoxyvinyl phosphonates: Facile synthesis via catalytic acylation of dialkyl phosphites

✍ Scribed by Nikolay I. Tyryshkin; Alexandra V. Fuzshenokova; Andrey N. Vedernikov; Boris N. Solomonov

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
373 KB
Volume
3
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

A new and facile method of synthesis of 1‐acetoxyvinyl phosphonates (2) has been found. Dialkyl phosphites react readily with acetic anhydride in acetonitrile solution in the presence of catalysts to produce 2 and acylphosphonates (1) as a minor product. The most efficient catalysts are metal compounds of variable valency: iron(II), iron(III), and cobalt(II) chlorides. The same compounds catalyze transformation of 1 into 2 in an acetonitrile solution of acetic anhydride.

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## Abstract The addition of di‐(trimethylsilyl)phosphite to __N__,__N__′‐terephthalylidene‐alkyl‐(or aryl‐)amines resulted in 1,4‐phenylene‐bis‐(__N__‐alkylamino‐ methyl)‐phosphonic acids in moderate yields. The stereochemical behavior of such reactions was studied, and NMR studies demonstrated tha