摘要:
The nickel(0)- and iron(0)-promoted dechlorination of dimethyl 1,2-dichloro-3-vinylcyclobutane-1,2-dicarboxylate (1) to dimethyl 3-vinylcyclobutene-1,2-dicarboxylate (2) occurs faster in the trans isomer. Nickel(0) and nickel(I), but not iron(0), with promote the rearrangement of this vinylcyclobutene to dimethyl 1,4-cyclohexadiene-1,2-dicarboxylate (3). The effect of methyl substituents on these reactions indicate that the nickel must transfer to the vinyl group before the rearrangement can occur. It also was found that nickel will cleave exclusively the bond between an sp2- and an sp3-hybridized carbon.