SELECTIVE BROMOCHLORINATION OF ENDO-1,4-DIBROMOTRICYCLO[5.2.1.0(2,6)]DECA-3,8-DIENE-5,10-DIONE 10-ETHYLENE ACETAL AT THE CONJUGATED CARBON-CARBON DOUBLE-BOND

Abstract

Exposure of (1) to bromine in thionyl chloride/ dimethylformamide produced (5), the result of regio- and stereo-selective addition of bromine chloride across the carbonyl-conjugated double bond. The structure of (5) was determined by X-ray crystallography, and its mode of formation is discussed in terms of the carbonyl attack mechanism.