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The N-chloromethyl group of 1-(chloromethyl)benzotriazole undergoes nucleophilic substitution by carbon, nitrogen, phosphorus, oxygen, and sulphur nucleophiles. α-Lithiation was achieved in high yield in 1-phenylthiomethyl-, 1-phenylsulphinylmethyl-, and 1-(phenylstilphonylmethyl)benzotriazoles and the lithio derivatives reacted with a variety of electrophiles. New benzotriazolium salts were prepared by quaternization of the N-3 nitrogen with methyl iodide.
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Katritzky et al. (1987) studied this question.
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