Reactions of aryl sulfides and phosphorus (V) esters of thiols with acidic hydrogen peroxide

CA Bunton, HJ Foroudian, ND Gillitt…

Index: Bunton; Foroudian; Gillitt; Kumar Canadian Journal of Chemistry, 1999 , vol. 77, # 5-6 p. 895 - 902

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Citation Number: 4

Abstract

Oxidations of sulfides and phosphorus (V) esters of thiols by H2O2 are catalyzed by H2SO4 and HClO4. Sulfides are 4-ZC6H4SMe, 1a-1e, respectively, Z= MeO, Me, H, Cl, NO2; PhSCH2CH2Cl, 2, Ph2S, 3, and the esters are Ph (R) PO⊙ SEt, 4a, 4b, R= Ph, EtO. Electron donation by Z moderately accelerates reaction, but the sulfides are much more reactive than the esters. Reactions are first order in H2O2 and substrate, and second-order rate ...