Iodohydroxylation of alkylidenecyclopropanes. An efficient synthesis of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives

A variety of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives were readily prepared in good to excellent yields via the simple iodohydroxylation reaction of alkylidenecyclopropanes with I-2 and H2O. An unexpected rearrangement to :give 4-hydroxy-1,2-diphenyl-butan-1-one derivatives was observed compared to the halohydroxylation products.