The acyloin condensation. Synthesis of a [4,2,2]-propellane (tricyclo[4,2,2,01,6]decane)1 derivative
Abstract
Acyloin condensation of dimethyl bicyclo-[4,2,0]octane-1,6-dicarboxylate in the presence of chlorotrimethylsilane produces 7,8-bis(trimethylsilyloxy)-[4,2,2]propell-7-ene (25–40%) and the bis-(trimethylsilyloxy)-dimethoxy-keten acetal of 1,4-cyclo-octane dicarboxylate (40–58%); solvolysis of the propellane in weakly acidic methanol gave 1-methoxy-8-hydroxybicyclo[4,2,2]decane-7-one by apparent homoconjugate attack at the central carbon–carbon bond.