Syntheses based on mercaptobenzthiazole, mercaptobenzoxazole, and mercaptobenzimidazole
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The vinylation reaction of 2-mercaptobenzoxazole and 2-mercaptobenzimidazole is studied.
A number of sulfides and sulfones with sulfur atoms in the side chain, are prepared under reaction conditions developed on the basis of the heterocyclic vinyl sulfides.
Together with the usual free radical addition of thiols to the C=C double bonds of the prepared vinyl sulfides, the unexpected reaction of substitution of the S-vinyl group by the thiophenyl radical was found in the case of 2-benzimidazolyl vinyl sulfide.
The sulfur atom adjacent to the oxazole ring in 2-benzoxazolyl vinyl sulfide in contrast to 2-benzimidazolyl vinyl sulfide is not oxidized to the sulfone under mild conditions; under more vigorous conditions cleavage occurs with the formation of 2-hydroxybenzoxazole.
KeywordsSulfide Thiol Sulfur Atom Radical Addition Oxazole
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