An Improved Procedure for the Conversion of Carbonyl Compounds to ?,?-Unsaturated Carboxylic Acids

1 January 1978

journal article
research article
Published by Taylor & Francis in Synthetic Communications

Vol. 8 (7) , 463-468
https://doi.org/10.1080/00397917808063573

Abstract

The two carbon homologation of aldehydes and ketones to give α,β-unsaturated carboxylic acids is often carried out via the corresponding ester using metallated phosphonate reagents² (1) (Equation I). When alkyl esters (la) are employed problems are sometimes encountered in the hydrolysis step due to acid or base sensitivity but these problems can be overcome using the silyl ester (lb)³.

Keywords

This publication has 2 references indexed in Scilit:

Olefin synthesis with organic phosphonate carbanions
Chemical Reviews, 1974
Reaktionen mit Phosphinalkylenen, XV. Eine Synthese der „Königinnensubstanz”︁ und der trans‐10‐Hydroxy‐decen‐(2)‐säure‐(1) (royal jelly acid)
European Journal of Organic Chemistry, 1966