Fast and Highly Efficient Solid State Oxidation of Thiols.docVIP

Molecules 2007, 12, 694-702 molecules ISSN 1420-3049 Full Paper Fast and Highly Efficient Solid State Oxidation of Thiols Morteza Montazerozohori*, Shiva Joohari, Bahador Karami and Nasrin Haghighat Department of Chemistry, Yasouj University, Yasouj 75918-74831, P. O. Box-35, Iran * Author to whom correspondence should be addressed; E-mail: mmzohori@mail.yu.ac.ir; mmzohory@ Received: 22 January 2007; in revised form: 13 February 2007 / Accepted: 26 February 2007 / Published: 31 March 2007 Abstract: A fast and efficient solid state method for the chemoselective room temperature oxidative coupling of thiols to afford their corresponding disulfides using inexpensive and readily available moist sodium periodate as the reagent is described. The reaction was applicable to a variety of thiols giving high yields after short reaction times. Comparison of yield/time ratios of this method with some of those reported in the literature shows the superiority of this reagent over others under these conditions. Keywords: Solid state reaction, oxidation, periodate, thiols, disulfides. Introduction Oxidation of thiols to the corresponding disulfides is a characteristic functional group transformation, in which further oxidation(s) of the products to give disulfide S-oxides (thiolsulfinates), disulfide S-dioxides (thiolsulfonates), and sulfonic acids are possible, and consequently, considerable research has gone into controlling the initial oxidation. Weak S-S bonds in the disulfide products leads to high reactivity [1] and in natural products, the presence of these moieties and related cyclic analogues are associated with interesting biological activities and DNA- cleaving properties [2]. The vital role of the thiols and disulfides in living systems is due to their interconversion reactions so therefore oxidative coupling of the th