Selenium dioxide reaction of substituted diphenacyl sulfides: generation of α -ketoacids

Abstract

The attempted selenium dioxide oxidation of substituted diphenacyl sulfides in anticipation of further functionalization led to a series of α -ketoacids 3 via oxidation followed by C‒S bond cleavage. Two minor products, 5 and 6, have also been isolated and a mechanistic pathway for the formation of 3, 5 and 6 has been proposed.

GRAPHICAL ABSTRACT

Keywords:

• diphenacyl sulfides
• α-ketoacids
• oxidation
• 2-oxo-2-arylacetic thioanhydride
• selenium dioxide

Acknowledgements

The authors thank DST, New Delhi, for assistance under the IRHPA program for providing funds for creating an NMR facility. Financial supports from CSIR-JRF, New Delhi, are gratefully acknowledged.

Notes

1. Crystal data for 3b: Empirical formula C₈H₇ClO₄, Formula weight 202.59, triclinic, space group P-1, Unit cell = 5.8696(9) Å=78.149(9)° b = 7.8565(12) Å,= 89.719(12)° c = 18.475(3) Å = 87.365(8)°, Volume 832.9(2) Å3, Z = 4, f(000) = 416, R(reflections) = 0.0311(1826), wR2(reflections) = 0.0783( 2416), and Goodness-of-fit on F2 1.089. Complete crystallographic data, as a CIF file, have been deposited with the Cambridge Crystallographic Data Centre (CCDC number is 908749).