Synthesis of TKX-50 via 2-Methoxyisopropyl-Protected Diazidoglyoxime as an Insensitive Intermediate

초록

A safe synthesis of dihydroxylammonium 5,5 '-bistetrazole-1,1 '-diolate (TKX-50) has been achieved by using 2-methoxyisopropyl-protected diazidoglyoxime (MIP-DAzG) as an insensitive intermediate. The MIP group acted as a protecting group, which was quantitatively introduced into dichloroglyoxime without the need for any additives, and effectively removed during the course of the cyclization reaction used to construct the 5,5 '-bistetrazole-1,1 '-diol moiety under acidic conditions. Notably, the sensitivity results obtained for MIP-DAzG were significantly lower than those of the DAzG intermediate used in the previously reported synthesis of TKX-50. Furthermore, the sensitivity studies on MIP-DAzG indicated that the sensitivity of protected DAzG was affected by the steric hindrance around the hydroxyl group in DAzG caused by the protecting group.

키워드