Alkylation of esters. An ester enolate as a possible ambident anion

1 January 1971

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society D: Chemical Communications

No. 16,p. 951-952
https://doi.org/10.1039/c29710000951

Abstract

Alkylation of methyl O-(tetrahydropyran-2-yl)-mandelate in dimethyl sulphoxide was shown to produce transesterification products at 80° whereas normal C-alkylation was observed at 25°.

Keywords

ESTERS
ESTER ENOLATE
ANION ALKYLATION
DIMETHYL SULPHOXIDE
AMBIDENT ANION
PRODUCE TRANSESTERIFICATION
TRANSESTERIFICATION PRODUCTS