Organometallic compounds in organic synthesis. Part 14. Tricarbonyliron as lateral control group in the selective alkaline hydrolysis of some cyclohexa-1,3-diene carboxylic esters

Abstract

Alkaline hydrolyses of a number of methoxycarbonyl derivatives of cyclohexa-1,3-diene–Fe(CO)₃ have been used as indices of steric and electronic effects on reactivities of the ester groups. A β-CO₂Me or a 1-CO₂Me group is resistant to hydrolysis for steric and electronic reasons, respectively. A number of substituted esters are examined and, with dicarboxylic esters complexation used successfully to enable half hydrolyses, which cannot readily be accomplished with the parent esters.