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A Novel Recyclable Sulfur Monoxide Transfer Reagent

Richard S. Grainger, Alberto Procopio and Jonathan W. Steed

*Department of Chemistry, King’s College London, Strand, London WC2R 2LS, U.K., Email:

R. S. Grainger, A. Procopio, J. W. Steed, Org. Lett., 2001, 3, 3565-3568.

DOI: 10.1021/ol016678g (free Supporting Information)


Reduction of a disulfide and subsequent trapping with thionyl chloride provides a trisulfide oxide. Heating this trisulfide oxide in the presence of dienes results in transfer of sulfur monoxide to form cyclic unsaturated sulfoxides in very good yields, along with recovery of the starting disulfide.

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There is a follow-up full paper to this communication:

Sulfur Monoxide Transfer from peri-Substituted Trisulfide-2-oxides to Dienes: Substituent Effects, Mechanistic Studies and Application in Thiophene Synthesis

R. S. Grainger, B. Patel, B. M. Kariuki, L. Male, N. Spencer, J. Am. Chem. Soc., 2011, 133, 5843-5852.

Richard S. Grainger, April 28, 2021

Key Words


ID: J54-Y2001