K. Brewster, R. Chittenden, R. Pinder
1972
Citations
0
Influential Citations
2
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
Reformatsky reactions of ethyl bromoacetate with indan-1-ones usually gave mixtures of the endo- and exo-unsaturated esters, but the reaction with 5,6-dimethoxyindan-1-one gave solely the exo-isomer. Hydrolysis of the esters from the title indan-1-ones gave mixtures of the isomeric acids, except in the last case, when 5-methoxy-indene-3-acetic acid alone was obtained. It is concluded that the functional role of the aryl substituent in providing an extended conjugated system favours exo-unsaturation.