Bromination of 3-cyclohexene-1-carboxylic acid, epoxydation of methyl 3-cyclohexene-1-carboxylate and opening of methyl cis- and trans-3,4-epoxycyclohexane-1-carboxylate:Stereochemical results

Add time:09/01/2019    Source:sciencedirect.com

Bromination of 3-cyclohexene-1-carboxylic acid (1) gives mixtures of the trans-dibromo-derivatives 3 and 4 and cis-3-hydroxy-trans-bromocyclohexane-1-carboxylic acid lactone (5). Lactone 5 is obtained by brominating 1 in the presence of triethylamine, showing that halogen preferentially attacks the double bond anti with respect to the carboxyl group. Epoxydation of the methyl ester of 1 also takes place prevalently anti to the methoxycarbonyl group. Ring opening of methyl cis-3,4-epoxycyclohexane-1-carboxylate (7) with hydrogen bromide gives methyl trans-3-bromo-cis-4-hydroxy- (13) and cis-3-hydroxy-trans-bromocyclohexane-1-carboxylate (6). Similar opening of methyl trans-3,4-epoxycyclohexane-1-carboxylate (11) affords methyl trans-3-hydroxy-cis-4-bromocyclohexane-1-carboxylate (14). The steric course of these reactions is ascribed to the effect of the electron-withdrawing substituent.

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