Stereochemistry of cyclic compounds Communication 9. Condensation of 1-vinyl-1-cyclohexene with methyl acrylate

Abstract

1. A study was made of the condensation of 1-vinyl-1-cyclohexene with methyl acrylate. Hydrolysis of the product gives a mixture of syn- and anti-1,2,3,5,6,7,8,8a-octahydro-1-naphthole acids (III) and (IV)., and it was shown that with rise in the condensation temperature the amount of anti isomer (IV) increases with simultaneous decrease in the amount of syn isomer (III). 2. The spatial configuration of syn- and anti-1,2,3,5,6,7,8,8a-octahydro-1-naphthoic acids (III) and (IV) were established by converting them into known decahydro-1-naphthylamines; they are epimers with respect to the hydrogen at C-8a. 3. It was shown that the hydrogenation of the isomeric acids (III) and (IV), and also of the corresponding esters (I) and (II), is sterically selective and occurs from the side opposite to the carboxyl with formation of acids (V) and (VIII), and also esters (VI) and (IX), of the cis- and trans-decahydronaphthalene series respectively. 4. It was shown that the isomeric syn and anti acids (III) and (IV) behave differently under lactonization conditions. An examination of molecular models has enabled us to explain the stereochemical pecularities of the epimers that we have obtained.