Syntheses of 3,3-Disubstituted 2-Arylacrylic Acids

Publisher Website
Google Scholar
Abstract
The syntheses of several 3,3-disubstituted 2-arylacrylic acids are described. The Wittig reaction between arylglyoxylic esters and isopropylidenetriphenylphosphorane provides an efficient route to 2-aryl-3-methylcrotonic esters. Bromination of these esters with N-bromosuccinimide gives a mixture of the 3-bromomethyl-2-arylcrotonic esters and -2-arylisocrotonic esters. The 3-bromomethylcrotonic esters upon heating cyclize to lactones. Also prepared were 2-aryl-3-azidomethylisocrotonic acids and 3-aminomethyl-2-phenylisocrotonic acid. A stereospecific route to 3-azidomethyl-2-phenylisocrotonic acid and cis-3-azidomethyl-2-phenyl-2-pentenoic acid has been developed starting from α-methyl- and α-ethylcinnamic esters.

This publication has 0 references indexed in Scilit: