Bromination reactions of 2-substituted derivatives of 7-oxabicyclo[2.2.1 ]hept-5-ene
Abstract
The bromination reactions of the endocyclic double bond of some 2-substituted derivatives of 7-oxabicyclo[2.2.1]hept-5-ene with bromine and N-bromosuccinimide in different conditions have been studied. The stereochemical outcome of the reaction and the nature of the products (derived from addition, rearrangement and/or fragmentation) is discussed as a function of the reaction conditions and of the nature of the substituent on C-2. In the case of 2-exo-methyl-7-oxabicyclo[2.2.1 ] hept-5-en-2-endo-ol, the reaction allows for a straightforward synthesis of 2-exo bromo-5-exo-methyl-4,7-dioxatricyclo[3.2.1.03,6] octane.