Organic Chemistry Portal



TAPC-Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides

Kiumars Bahrami*, Mohammad M. Khodaei* and Mehdi Sheikh Arabi

*Department of Chemistry, Razi University, Kermanshah 67149-67346, Iran, Email:,

K. Bahrami, M. M. Khodaei, M. S. Arabi, J. Org. Chem., 2010, 75, 6208-6213.

DOI: 10.1021/jo1011784


1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC) is an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.

see article for more examples

Proposed Mechanism for the Oxidation of Sulfides

Proposed Mechanism for the Deoxygenation of Sulfoxides

TAPC-Promoted Synthesis of Sulfonyl Chlorides from Sulfonic Acids

K. Bahrami, Synlett, 2011, 2671-2674.

H2O2/Tf2O System: An Efficient Oxidizing Reagent for Selective Oxidation of Sulfanes

M. M. Khodaei, K. Bahrami, A. Karimi, Synthesis, 2008, 1682-1684.

Mild and Efficient Deoxygenation of Sulfoxides to Sulfides with Triflic Anhydride/Potassium Iodide Reagent System

K. Bahrami, M. M. Khodaei, A. Karimi, Synthesis, 2008, 2543-2546.

Key Words

Sulfoxides, Sulfones, Deoxygenation, Green Chemistry

ID: J42-Y2010-2540