All articles of this category Benzylidene dihydrothiazoles undergo DDQ-promoted hydrogen abstraction to yield an original ambivalent electrophilic intermediate. Treated with nucleophiles this covalent intermediate undergoes two possible substitution reactions one at the 5-methyl position and one at the DDHQ aromatic center. For a given benzylidene dihydrothiazole the ratio of the two products depends on the nature of the nucleophile. electron transfer - heterocycles - nucleophilic addition - oxidation - quinone
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Vanier et al. (2001) studied this question.
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