The Journal of Organic Chemistry

Kinetics of the aqueous periodate oxidation of aliphatic disulfides and thioethers

BJ Evans, JT Doi, WK Musker

Index: Evans, Brian J.; Takahashi Doi, Joyce; Musker, W. Kenneth Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2580 - 2586

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Citation Number: 17

Abstract

A colorimetric method was developed which uses 2, 2'-azinobis (3-ethylbenzothiazoline-6- sulfonic acid)(ABTS) to determine the concentrations of periodate. The y-substituted amine- disulfide lb consumes 4 equiv of periodate at a rate which is accelerated 100-fold over that of 4, 4'-dithiodibutanol (IC) and forms the cyclic sulfinamide 3 and sulfonamide 4. To account for the stoichiometry and acceleration, we have proposed intermediates in which a ...