The thermal, photochemical, base-catalyzed, and Lewis acid-catalyzed reactivity of 2- azidotetrahydrothiophene (1 a) and the related α-azidosulfoxide and sulfone have been found to lead to a number of interesting rearrangement products. The 13C nmr data for these compounds are also reported and discussed and the results of attempted deoxygenation of the α-azidosulfoxide 1 b with a variety of reagents are compared.
