Halohydroxylation of alkylidenecyclopropanes using N-halosuccinimide (NXS) as the halogen source: an efficient synthesis of halocyclopropylmethanol and 3-halobut-3-en-1-ol derivatives

A variety of halocyclopropyl-methanol and 3-halo-but-3-en-1-ol derivatives were prepared in moderate to excellent yields via the simple halohydroxylation reaction of alkylidenecyclopropanes with convenient and mild sources of electrophilic halogen NXS (X = I, Br, Cl, F) and H2O. A plausible mechanism for the halohydroxylation has been proposed.