The stereochemistry of THIANE (cas 1413-51-0) oxidation : Participation of neighboring groups
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Add time:09/30/2019 Source:sciencedirect.com
THIANE (cas 1413-51-0)s not containing 4-OH or 4-CO groups are oxidized by wet bromine predominantly to equatorial thiane 1-oxides. The reaction is assumed to proceed by way of an equatorial electrophilic attack by hypobromous acid at the S atom. An electronic interpretation is given of the steric course of electrophilic reactions at the S atom in thianes. With thianes containing 4-OH or 4-CO groups, oxidation to thiane 1-oxides by wet bromine or by t-butyl hypochlorite resulted in a reversal of the usual stereospecificities of these reagents. A two step process involving participation by the 4-substituents is given to account for the different steric course of the reactions in these cases.
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