The Journal of Organic Chemistry

Reactions of diethoxytriphenylphosphorane with diastereoisomeric 3-methylcyclohexane-1, 2-diols. Control of regioselectivity by methyl substitution during …

PL Robinson, SA Evans Jr

Index: Robinson, Philip L.; Evans, Slayton A. Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3860 - 3863

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Citation Number: 15

Abstract

The diastereoisomeric 3-methylcyclohexane-trans-1, 2-diols undergo cyclodehydration with diethoxytriphenylphosphorane (DTPP) to afford the cis-and trans-3-methylcyclohexene oxides. The ratio of cis and trans epoxides is best explained by assuming preferential phosphoranylation of the C1 hydroxyl group followed by" 3-exo-tet" alkoxide displacement of triphenylphosphine oxide. The diastereoisomers of S-methylcyclohexane-cis-1, 2-diol ...

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