Abstract: 1. A study was made of the diene condensation of 1-vinyl-l-cyclohexene with malefic anhydride. It gives the syn-cis and anti-cis anhydries (I) and (X) for the proportions of 10 : 1. These isomers differ in the dispositions of the hydrogen at C-8a. 2. The thermal transformation of the syn-cis anhydride (I) into the anti-cis anhydride (X) was effected, and the corresponding isomeric acids (II) and (XI) and isomeric esters (III) and (XII) were prepared. 3. It was shown that the hydrogenation of derivatives both of the syn-cis series (I, II, III) and also of the anti-cis series (X,XI,XII) proceeds in a sterically selective manner: hydrogen adds from the least screened side (opposite to the carboxyl groups) with formation of derivatives of the cis- and trans-decahydronapthalene series respectively, 4. An examination of molecular models has enabled us to explain: the spatial configurations of the adducts obtained, (I) and (X), and also the steric selectivity of the hydrogenation of these and other compounds obtained.

Cite: Nazarov I.N. , Kucherov V.F. , Andreev V.M.
Stereochemistry of cyclic compounds. Communication 10. Stereochemistry of the diene condensation of 1-vinyl-1-cyclohexene with maleic anhydride
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1956. V.5. N6. P.727-732. DOI: 10.1007/bf01178936 OpenAlex

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W2017097231

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