Silica gel triggered transformations of 3-methylenecyclopropylmethyl sulfonates to 3-methylenecyclobutyl analogues: experimental and computational studies.

Methylenecyclopropylcarbinols treated with sulfonyl chloride and Et(3)N form the sulfonated products in almost quantitative yields, which can be transformed to the corresponding 3-methylenecyclobutyl sulfonates with silica gel chromatography work-up. The rational explanation was proposed on the basis of computational studies.