LIGAND COUPLING THROUGH ?-SULFURANE --- COMPLETE RETENTION OF GEOMETRIC CONFIGURATION OF ALLYLIC AND VINYLIC GROUPS IN THE REACTIONS OF ALLYLIC AND VINYLIC SULFOXIDES WITH GRIGNARD REAGENTS

Article abstract of DOI:10.1016/S0040-4039(00)80518-3

The reaction of p-benzenesulfonylphenyl crotyl sulfoxide with Grignard reagents is considered to proceed via formation of an incipient ?-sulfurane to afford the coupling product, p-benzenesulfonyl-crotylbenzene, in which the geometric configuration of crotyl group was completely preserved.No rearrangement was observed in the coupling reaction of p-benzenesulfonylphenyl α-methylallyl sulfoxide.Such a complete retention of geometric configuration was also found in the reactions of 2-pyridyl and p-benzenesulfonylphenyl styryl sulfoxides with Grignard reagents.