Reactions of an Allylic Sulfide, Sulfoxide, and Sulfone with Singlet Oxygen. The Observation of a Remarkable Diastereoselective Oxidation

Article abstract of DOI:10.1021/ja00197a044

The reactions of singlet oxygen with 1-<(4-methylphenyl)sulfinyl>-2,3-dimethyl-2-butene (6), 1-<(4-methylphenyl)sulfonyl>-2,3-dimethyl-2-butene (7), and 2,3-dimethyl-2-butenyl p-methylphenyl sulfide (8) have been examined.The formation of transient intermediates and products in the reaction of 8 have been followed as a function of extent of reaction and a remarkable diastereoselective reaction has been uncovered.The implications of this discovery for the mechanism of sulfide oxidation is discussed.