Reaction of Ketene Silyl Acetals with Unsaturated Nitrites in the Presence of Titanium Tetrachloride

Abstract

The reaction of ketene alkyl silyl acetals with acrylonitrile in the presence of titanium tetrachloride in dichloromethane at -80°C leads to coupled compounds. Formation of these products can be explained by the transformation of ketene acetals into enoxy radicals trapping of these radicals by acrylonitrile and then dimerization. With bisketene acetals derived from glutarate and pimelate a ring closure reaction was observed leading to the formation of cyclopentane and cyclononane derivatives. No cyclisation was observed with ketene acetals derived from higher diesters.