BROMINATION OF EXO-TRICYCLO[3.2.2.0(2,4)]NON-6-ENE

In carbon tetrachloride reaction of 1 with bromine occurs at the doubl e bond and is favored from the less hindered face, anti to the cyclopr opane ring, to give 2 and 3 (2:1) over reaction from the syn face or a t the corner of the cyclopropane to give 5. In the solvent methanol, c orner attack of bromine at the cycloproane to give 30, 16, 17, and 37 competes with reaction at the double bond anti to the cyclopropane to give 18, 19, and 2.