Dihaloimidazolidinediones as Versatile Halodehydrating Agents

Dihaloimidazolidinediones containing geminal dibromides, dichlorides, or diiodides were synthesized and used to transform various alcohols to their corresponding alkyl halides in high yields and under mild conditions. High functional group tolerance and, in many cases, high selectivities were observed. Efforts toward elucidating the mechanism revealed that significant charge build-up may occur at the eventual halogen containing carbon nucleus prior to substitution.