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Abstract
Tetrazole Compounds. 4. Alkylation of 1‐Aryl‐5‐(2‐dimethylamino‐vinyl)‐1 H‐tetrazolesAlkylation of 1‐aryl‐5‐(2‐dimethylamino‐vinyl)‐1 H‐tetrazoles 1 with dialkyl sulfates or alkyl iodides yields mainly 4‐alkyl‐1‐aryl‐5‐(2‐dimethylamino‐vinyl)‐1 H‐tetrazolium salts which can be isolated free from isomers by separation as perchlorates 2. The reaction proceeds with retention of the E configuration of the vinyl group. In contrast to 1 the methyl groups of the dimethylamino substituent in 2 are magnetically non‐equivalent indicating restricted rotation of this residue. On heating 2 with aqueous mineral acids the dimethylaminovinyl moiety undergoes degradation to a methyl group affording 4‐alkyl‐1‐aryl‐5‐methyl‐1 H‐tetrazolium salts 4, the structure of which was confirmed by independent synthesis. With hot aqueous alkali hydroxide 2 reacts under ring cleavage to give aryl azide. — 1H n.m.r. and u.v. spectroscopic data of the tetrazolium salts 2 and 4 are reported.
Published Version
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