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

Alkyl iodides give products from the neopentyl rearrangement on reaction wi th xenon difluoride. Neopentyl iodide performs a double rearrangement and y ields a gem-difluoro product, 2,2-difluoro-3-methylbutane. Studies of the m echanism show that an alkene intermediate is involved in the double rearran gement process. Alkenes can be substituted as substrates in reaction with x enon difluoride-iodine to give gem-difluoro products. C-13 Labeling verifie s the skeletal rearrangement process. (C) 2000 Elsevier Science S.A. All ri ghts reserved.