Allyl and benzyl iodides by the anomalous action of iodotrimethylsilane

Iodotrimethylsilane (TMSI), routinely used for the dealkylation of ethers and esters, has been found to efficiently convert allyl and benzyl phosphotriesters into the corresponding iodides under mild, Brønsted-neutral conditions. In contrast, alkyl and aryl phosphotriesters were dealkylated to the corresponding phosphates under identical conditions.