Abstract
The addition of 2-bromoethanesulfonyl bromide to 1-bromotricyclo[4.1.0.02,7]heptane at the C1–C7 central bicyclobutane bond follows a radical mechanism to give 1:1 adduct with a bicyclo[3.1.1]heptane structure. Treatment of the adduct with triethylamine leads to the formation of vinyl sulfone as a result of 1,2-dehydrobromination, and its reaction with 2 equiv of sodium methoxide involves 1,2- and 1,3-dehydrobromination to afford 7-bromo-1-(ethenesulfonyl)tricyclo[4.1.0.02,7]heptane. The latter is capable of reacting with sodium methoxide and sodium methanesulfonate to form nucleophilic addition products.
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