Adamantylazoles: XIV. Acid-catalyzed alkylation of 5-aminotetrazoles with tertiary alcohols

Alkylation of 5-aminotetrazole with tert-butyl alcohol or adamantan-1-ol in sulfuric acid gave a mixture of isomeric N ¹- and N ²-alkyl derivatives, as well as 1,3-dialkyl-5-aminotetrazolium salt. Adamantylation of 1-substituted 5-aminotetrazoles led to the formation of mixtures of 1,3- and 1,4-disubstituted 5-aminotetrazolium salts which can be converted into the corresponding free bases.