A one pot conversion of alcohols to disuhides in good yields via the activation of a hydroxyl group with DCC or P(NMez)J / CC14 followed by treatment with benzyltriethylammonium tetrathiomolybdate is reported 0 1999 Elsevier Science Ltd. All rights reserved. Ke,vwrds; alcohols. amino acids. disulfides. macroqcles Disultides are a very important class of compounds in chemistry as well as biology.' Because of their importance, their synthesis assumes significance and several methods are known for this purpose. Most of the methods involve the conversion of alkyl halides or sulfonates into the corresponding thiols followed by oxidation.' Since halides and sulfonates are made from alcohols and sometimes the conversion of alcohols to halides or sulfonates are troublesome, direct conversion of an alcohol to the corresponding disultide will be a significantly useful methodology We have previously shown that alkyl halides and tosylates react with benzyltriethylammonium tetrathiomolybdate [(PhCHsNEts)sMoS4], 1 to give alkyl disultides in good yield.' We wanted to extend this methodology for the conversion of alcohols to disultides (ROH -+ RSSR). In order to apply the sulIIrr transfer reaction mediated by tetrathiomolybdate, 1 for this transformation we decided to adopt the m situ activation of alcohols using either DCC4 or P(NMe2)J/CCh5 which can be tinther treated with tetrathiomolybdate, 1 to yield the corresponding disulfides (Scheme 1 & 2).
Benzyl alcohol, 2 was chosen as the model substrate and was treated with dicyclohexyl carbodi-