REDUCTION OF SOME POLYHALOGENATO- AND POLYACETOXYALLYLIC COMPOUNDS WITH TRIBUTYLTIN HYDRIDE IN THE PRESENCE OR ABSENCE OF A PALLADIUM CATALYST I. REDUCTION OF DICHLORO- AND DIACETOXY-PROPENES

Article abstract of DOI:10.1016/S0022-328X(00)99713-4

Radical-promoted tributyltin hydride reduction of 3,3-dichloropropene, (Z)-1,3-dichloropropene, or (E)-1,3-dichloropropene yields a mixture of the three possible regio-stereoisomeric monochloropropenes.The palladium-catalyzed reduction yields regiospecifically the two stereoisomeric 1-chloropropenes with a Z/E ratio which remains constant whatever the starting dichloropropene but which is not the thermodynamic ratio.The results are against a radical mechanism and strongly support a polar ?-allyl mechanism for the catalytic reactions.