Abstract
The gem-dibromocyclopropanes trans-13,13-dibromobicyclo[10.1.0]tridecadiene-(4t,8t) ( 1) and trans-13,13-dibromobicyclo[10.1.0]tridecane ( 2) undergo facile ring expansion during silver ion assisted solvolysis. Reaction of 1 and 2 with methanolic silver nitrate gave high yields of 1-methoxy-2-bromo-cyclotridecatriene-(2t,6t,10t) ( 3), and 1-methoxy-2-bromo-cyclotridecene-(2t) ( 5) respectively, while reaction with aqueous silver nitrate yielded 2-bromo-cyclotridecatriene-(2t,6t,10t)-ol ( 4), and 2-bromo-cyclo-tridecene-(2t)-ol ( 6) respectively. In no case were products found with cis double bonds. The stereochemistry of 3–6 was determined by NMR spectroscopy and by reduction.
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