Tetrahedron

The favorskii rearrangement of dichlorinated methylketones

N Schamp, N De Kimpe, W Coppens

Index: Schamp,N. et al. Tetrahedron, 1975 , vol. 31, p. 2081 - 2087

Full Text: HTML

Citation Number: 22

Abstract

Twenty-two dichlorinated methylketones have been submitted to Favorskii rearrangement in NaOMe MeOH. Distribution of products is strongly dependent on substitution. Primary dichloromethyl-ketones (R2= H) gave rise to Favorskii esters only. Results are explained by a cyclopropanone intermediate, which is formed stereospecifically by disrotative closure of a delocalized zwitter-ion. Opening of the cyclopropanone intermediate is affected by steric ...