Decomposition d'hypobromites prepares par action de l'oxyde de mercure et du brome sur des alcools bicycliques pontes

Hydrobromites of bridged bicyclic alcohols have been decomposed to yield tetrahydrofuran-type ethers as well as fragmentation products. The latter results from the cleavage of the carbon-carbon bond α, β to the hydroxyl group. In the case of 3-hydroxy-3-methyl bicyclo[3.2.1]octane, conjugated ketones and brominated olefins are formed, whereas tetrahydrofuran-type ethers are formed only under different experimental conditions different from those applicable to general cases. The reaction mechanisms have been established. The influence of the various reaction parameters has been studied in order to obtain selectively either tetrahydrofuran-type ethers or a mixture of conjugated ketones and brominated olefins.