Abstract
Base-catalyzed condensation of 10-methylenecamphor with diethyl oxalate gave the corresponding (Z)-3-ethoxycarbonyl(hydroxy)methylene derivative which was converted into methyl ether and acetate. The Z-methyl ether undergoes isomerization into the E-methyl ether on treatment with N-bromosuccinimide in the presence of radical initiator [azobis(isobutyrodinitrile)]. (Z)-3-Ethoxycarbonyl(hydroxy)methylene-10-methylenecamphor smoothly reacts with N-bromosuccinimide to afford stereoisomeric 3-bromo derivatives.
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