DIASTEREOSELECTIVE SYNTHESIS OF 2,2′-THIOBIS- AND 2,2′-SULFONYLBIS- (1,3-DIARYLPROP-2-EN-1-ONES)—AN OXIDATIVE CONFIGURATIONAL SWITCH

Abstract

Synthesis of some heretofore unknown 2,2′-thiobis(1,3-diarylprop-2-en-1-ones) and their oxidation to new 2,2′-sulfonylbis(1,3-diarylprop-2-en-1-ones) are reported. The stereochemistry of the sulfides and sulfones assigned as (Z,Z)- and (E,E)- respectively by X-ray diffraction studies reveals a configurational switch from (Z,Z)- to (E,E)-during oxidation.

Keywords:

• 2,2′-Sulfonylbis(1,3-diarylprop-2-en-1-ones)
• 2,2′-thiobis(1,3-diarylprop-2-en-1-ones)
• bis(aroylmethyl) sulfides/sulfones
• nmr spectroscopic data
• stereochemistry

ACKNOWLEDGEMENTS

M.G. and S. R. thank the Correspondent and the Principal, Fatima College, Madurai-18 for facilities. S. P thanks CSIR, New Delhi for a Major Research Project, S. S. and S. P. thank U. G. C, New Delhi for funds under UGC-DRS program, DST, New Delhi for funds under FIST program and for funds for the purchase of a high resolution NMR instrument under DST-IRHPA program.