Rearrangement and double fluorination in the deiodinative fluorination of neopentyl iodide with xenon difluoride

Alkyl iodides give products from the neopentyl rearrangement on reaction with xenon difluoride. Neopentyl iodide performs a double rearrangement and yields a gem-difluoro product, 2,2-difluoro-3-methylbutane. Studies of the mechanism show that an alkene intermediate is involved in the double rearrangement process. Alkenes can be substituted as substrates in reaction with xenon difluoride–iodine to give gem-difluoro products. 13C Labeling verifies the skeletal rearrangement process.