IMPROVED SELECTIVE SYNTHESIS OF (Z)- AND (E)-1,2-BIS(PHENYLSULFONYL)-CHLOROETHYLENE

Abstract

The preparation of the title compounds (Z)- and (E)-1, which are synthetic substitutes for the unstable bis(phenylsulfonyl) acetylene and key reagents for the asymmetric preparation of polycyclic ketones, has been revisited and improved. Starting from inexpensive materials such as trichloroethylene, thiophenol, and hydrogen peroxide, (Z)- and (E)-1 are selectively obtained in multigram quantity in 52% overall yields.

ACKNOWLEDGMENT

Thanks are due to Mr. A. Canu of the University of Sassari for the microanalytical determinations. Work co-funded by MURST (Rome) within the national project “Stereoselezione in Sintesi Organica. Metodologie e Applicazioni.”