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Indole, carbazole, pyrrole, imidazole, benzimidazole, 2‐methyl‐ and 2‐phenylbenzimidazole, and 1, 2, 4‐triazole have each been converted into their N‐(benzotriazol‐1‐ylmethyl) derivatives. The pyrrole, indole, and carbazole adducts undergo smooth lithiation at the inter‐ring methylene group and subsequent reaction there with electrophiles. For the imidazole, benzimidazole, and triazole systems, lithiations at other molecular positions competed.

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Phenols and naphthols are benzotriazolylmethylated by 1‐(hydroxymethyl)‐1H‐benzotriazole (13) (a formaldehyde derivative) in the o‐ or (if both o‐positions are occupied) in the p‐position. The reaction can be extended to other aldehydes in the case of the naphthols. The methylene group in the o‐(benzotriazolylmethyl)phenols can be lithiated (but only after trimethylsilyl protection of the hydroxy group) and then substituted by various electrophiles. The benzotriazole residues in both the primary products and in their substituted derivatives can be displaced by the alkyl anions of Grignard reagents or by hydride ions allowing the elaboration of many new types of substituted phenols.