Alkylation of 5-(3,3-R,R′-2-oxido-1-triazeneoxymethyl)tetrazoles

Alkylation of 5-(3,3-R,R′-2-oxido-1-triazeneoxymethyl)tetrazole salts with iodomethane, dimethyl sulfate, chloroacetonitrile, and 1-chloromethoxy-3,3-dimethyl-1-triazene 2-oxide affords two isomers at positions 1 and 2 of the tetrazole ring as the major products. Tetrazoles containing oxymethyltriazene oxide groups at positions 5 and 1 (or 5 and 2) were synthesized for the first time.