Anodic oxidation. Part XIII. Products from bicyclo[2.2.1]hept-2-ene, bicyclo[2.2.1]hepta-2,5-diene, and tetracyclo[3.2.0.02,7.04,6]heptane

Abstract

Conditions are described under which electrolysis of bicyclo[2.2.1]hept-2-ene in methanolic sodium methoxide gives methyl tricyclo[2.2.1.0^2,6]heptan-3-yl carbonate, exo-2-methoxybicyclo[2.2.1]heptan-syn-7-yl methyl carbonate, its anti-isomer, and the corresponding 7-alcohols, and bicyclo[2.2.1]heptan-exo-2-yl methyl carbonate, in addition to the previously reported dimethoxylation products. Under the same conditions bicyclo[2.2.1]hepta-2,5-diene and tetracyclo[3.2.0.0^2,7.0^4,6]heptane each give as the major products exo-2,syn-7-dimethoxybicyclo[2.2.1]hept-5-ene, exo-3,endo-5-dimethoxytricyclo[2.2.1.0^2,6]heptane, and exo-3,exo-5-dimethoxytricyclo[2.2.1.0^2,6]heptane, but when bicyclo[2.2.1]hepta-2,5-diene is electrolysed in methanolic sodium methyl carbonate, methoxy-alcohols are again produced.