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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 24
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Original Articles

Synthesis of Novel 2‐Vinylcyclopropane Phosphonic Acids

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Pages 3679-3691 | Received 23 Nov 2005, Published online: 01 Dec 2006
 

Abstract

2‐Vinylcyclopropane‐1‐phosphonic acid diesters 1ad were synthesized by the reaction of trans‐1,4‐dibromo‐2‐butene with α‐substituted phosphonic acid diesters. Esterification of 1‐ethoxycarbonyl‐2‐vinylcyclopropane‐1‐carboxylic acid with dimethyl 2‐hydroxyethyl‐phosphonate gave the 2‐vinylcyclopropane phosphonic acid dimethylester 1e. The silylation of phosphonic acid diesters 1ae by halotrimethylsilanes followed by solvolysis with methanol or water resulted in the formation of phosphonic acids 2a–e. In the case of steric hinderance of the phosphoryl group, monoesters 3c,d were also formed. Furthermore, ethyl carboxylate 1b could be chemoselectively cleaved by aqueous potassium hydroxide to carboxylic acid 4.

Acknowledgment

The authors thank Margit Gruner from the Technical University of Dresden for performing the 2DNMR spectroscopic experiments and for the helpful discussions, and M. Maffei for providing 1d.

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