THE CLEMMENSEN REDUCTION OF ENOL ETHERS: CYCLOPROPYL ETHERS FROM MONO- AND DI-METHOXYCYCLOHEXA-1,4-DIENES

Article abstract of DOI:10.1016/S0040-4039(00)85915-8

Clemmensen reduction (zinc and hydrogen chloride in dry diethyl ether) of 1-methoxy- and 1,5-dimethoxy-cyclohexa-1,4-diene affords the cyclopropyl ethers, 1-methoxy- and 1,5-dimethoxy-bicyclo<3.1.0>hexane; in the presence of acetic anhydride, reduction of 6-acetyl-1-methoxy-6-methyl-cyclohexa-1,4-diene leads regiospecifically to 7-acetoxy-1-methoxy-6,7-dimethyl-bicyclo<4.1.0>hept-4-ene.