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13.30.4.2 Addition Reactions

DOI: 10.1055/sos-SD-013-01452

Brigas, A. F.Science of Synthesis, (200413904.

Tetrazoles are weak bases, pKa 3 to 4, and can be protonated by addition of sulfuric acid. As predicted by calculations,[‌239‌] protonation occurs preferentially at N4; this is similar to what is generally observed with alkylation, e.g. formation of 92 (Scheme 66).[‌152‌,‌240‌,‌241‌] For example, 2,5-diaryltetrazoles react with dimethyl sulfate at 80°C to give high yields of the corresponding 4N-methyl-quaternized tetrazole. The structure of the substituents, e.g. 5-substituted 1-vinyltetrazoles, and the nature or size of the alkylating agent can lead to some alkylation at N3.[‌242‌,‌243‌]

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