A highly practical protocol for preparing cyanomethyl ethers from aliphatic alcohols via their MEM ethers has been developed using trimethylsilyl cyanide in the presence of a Lewis acid. A number of Lewis acids were investigated, and ZnI2 was found to be the most effective for converting a variety of MEM ethers to the corresponding cyanomethyl ethers. Both bidentate coordination of ZnI2 with the MEM group and steric hindrance of the substrates play pivotal roles in this transformation.
Samala et al. (Fri,) studied this question.