A-Hydroxy sulfides

Many of these a-hydroxy sulfides can be cleaved by a reagent composed of lead tetraacetate, pyridine, and acetic acid in a molar ratio of about 2 4 3 per mole of substrate. A tran -diaxial arrangement is required and highly hindered a-hydro"Xy sulfides are not cleaved. 

Dibenzo[c, ] derivative (75) was reportedly obtained as a by-product in the reaction of a hydroxy sulfide with acetonitrile (Equation (40)) <74kgsi437, 74MI 921-02, 75Kgsi620>. Unfortunately, only limited information is available, precluding any analysis of this unique apparent [4 -t- 4] route to the 1,2-dithiocin ring system. 

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