Some attempts to use the modified acyloin reaction of Schräpler and Rühlmann for the synthesis of strained carbocylic systems
Abstract
Dimethyl trans-cyclopropane-1,2-diacetate (I) and dimethyl trans-oct-4-ene-1,8-dioate (II) failed to undergo cyclisation under the conditions of the modified acyloin reaction. Dimethyl cis- and trans-cyclopropane-1,2-dicarboxylate underwent reductive cleavage with formation of 1,5-dimethoxy-1,5-bis(trimethylsilyloxy)penta-1,4-diene (IV).