ChemInform Abstract: Tetrazole Compounds. Part 4. Alkylation of 1‐Aryl‐5‐(2‐dimethylamino‐vinyl)‐1H‐tetrazoles.

Abstract

Alkylation of the tetrazoles (I) with dialkyl sulfates (or, slightly less effective with alkyl iodides) yields mainly 4-substituted tetrazolium salts which can be isolated free from isomers by separation as perchlorates (III). The reaction proceeds with retention of the E configuration of the vinyl group. On heating (IIIa), (IIIb), (IIId) with aqueous mineral acids, degradation occurs affording the salts (IV), the structure of which is confirmed by independent synthesis. With hot aqueous alkali hydroxide, (III) react under ring cleavage to give respective aryl azides.