THE OXYMERCURATION OF 1,4-↑↑-METHYLENE-Δ5-CYCLOHEXENE-2-CARBOXYLIC ACIDS

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Abstract
The oxymercuration of 1,4-↑↑-methylene-Δ5-cyclohexene-2-↑-carboxylic acid yields two diastereomeric hydroxychloromercurials. Their configurations cannot be specified on the basis of information now available with certainty. The oxymercuration of 1,4-↑↑-methylene-Δ5-cyclohexene-2-↓-carboxylic acid also yields two diastereomers, which are designated as 6-↓-hydroxy-5-↓-chloromercuri-1,4-↑↑-methylenecyclohexane-2-↓-carboxylic acid, γ-lactone and 6-↓-hydroxy-5-↑-chloromercuri-1,4-↑↑-methylenecyclohexane-2-↓-dicarboxylic acid, γ-lactone because the former is more easily deoxymercurated than the latter and because their dipole moments match relatively the corresponding moments of the analogous dicarboxylic acid γ-lactones, the configurations of which have been proved chemically. This is the first instance where two diastereomers of opposite configuration have been shown to be formed in an oxymercuration.

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