SELECTIVE CARBON–CARBON BOND FORMING REACTIONS VIA <i>S</i>-ALLYL DITHIOCARBAMATES. REDUCTIVE DESULFURIZATION OF ALLYLIC DITHIOCARBAMATES

Abstract

Abstract A convenient method for the selective conversion of alkyl halides (R’X) to the olefins, R’CH=C(R)CH3, was established by α alkylation of the lithium salts of allylic dithiocarbamates (CH2=C(R)CH2SCSNMe2;R=H or Me) followed by reductive desulfurization of the α-coupled products with the specific Raney Ni. Dependence of regioselectivity in the reductive fission of the dithiocarbamate group upon both substrate and reducing agent is described in some details.