Stereochemistry of cyclic compounds

Summary

• 1. A study was made of the condensation of 1-(1-acetoxyvinyl)cyclohexene (I) with methyl acrylate, and it was shown that the ratio in which the epimeric adducts (II) and (III) are formed is dependent on the condensation temperature. It was shown that, in contrast of the case of the condensation of 1-vinylcyclohexene, the main product is the anti isomer (II), the amount of which diminishes with rise in temperature, there being a simultaneous increase in the yield of the isometric syn adduct (III).

• 2. By alkalin hydrolysis of the mixture of adducts (II) and (III), the isometric decahydro-4-1-naphthoic acids were isolated in the form of the tran-anti acid (IV) and the trans-syn ester (VII). The spatial configuration of these products were proved by Clemmensen reduction into the known isometric acids of the trans-decahydronaphtalene series (VIII) and (IX).