HYDROGEN IODIDE STRATEGY FOR ONE-POT PREPARATION OF ALLYLIC AZIDES, NITRILES, AND PHENYL SULFONES FROM ALLYLIC ALCOHOLS

Hydrogen iodide, HI, cleanly generated in situ from Me3SiCl/NaI and water in acetonitrile under mild conditions, was found to be an attractive reagent for the conversion of allylic alcohols into allylic iodides which serve as good allylic cation equivalent. Thus, treatment of allylic alcohols with Me3SiCl/NaI/H2O, followed by the substitution with N3-, CN-, and PhS02-ions in the same flask produced the corresponding allylic compounds bearing azide, cyano, and phenyl sulfonyl functionalities in fair yields. This method provides a useful procedure for the preparation of allylic compounds from easily available allylic alcohols. © 1990, American Chemical Society. All rights reserved.