Solvolysis of 10,10-dibromotricyclo[4,3,1,01,6]decane. Evidence for an intermediate bicyclo[4,3,1]dec-1(10)-ene derivative

Abstract

Both (3) and (9) readily undergo Ag⁺-promoted solvolysis in aqueous acetone solution to give monocyclic ketones [(6) and (11), respectively] as the major products; it seems likely that the latter compounds results from the fragmentation of highly-strained bicyclic intermediates [(7) and (10), respectively].