SELENOSULFONATION OF ALLENES AND SUBSEQUENT REARRANGEMENT OF THE ADDUCTS: A FACILE SYNTHETIC ROUTE TO β-ARYLSULFONYL-SUBSTITUTED ALLYLIC ALCOHOLS

Article abstract of DOI:10.1016/0040-4039(82)80132-9

Se-Phenyl areneselenosulfonates add readily to allenes in a highly regiospecific fashion (eq. 3) to give 5.Oxidation of the PhSe group in 5 to PhSe(O) is followed by <2,3>-sigmatropic rearrangement to 6 and hydrolysis of 6 to the β-arylsulfonyl-substituted allylic alcohol 7, thereby providing a simple, high-yield route to these interesting compounds.