Abstract
2-Bromoethanesulfonyl bromide reacts with tricyclo[4.1.0.02,7]heptane and 1-methyltricyclo[4.1.0.02,7]heptane according to a radical mechanism to give products of both anti and syn addition across the C1–C7 central bicyclobutane bond having a norpinane (bicyclo[3.1.1]heptane) structure. Treatment of the adducts with triethylamine leads to the formation of vinyl sulfones as a result of 1,2-dehydrobromination, and their reaction with sodium methoxide involves 1,2- and 1,3-dehydrobromination and nucleophilic addition, depending on the substrate structure and reactant ratio.
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