Halogenated Ketenes. 34. Cycloaddition of Halogenated Ketenes and Conjugated Trimethylsilyl Enol Ethers

Article abstract of DOI:10.1021/jo00320a018

The generation of dichloroketene and methylchloroketene by the triethylamine dehydrohalogenation of the respective acid chlorides in the presence of conjugated trimethylsilyl enol ethers yields functionalized cyclobutanones with high regioselectivity.Both cross-conjugated and linear-conjugated trimethylsilyl enol ethers were found to yield <2 + 2> cycloaddition products in good yield.