Construction of an All-Bridge Carbon-Oxidized 2-Azaadamantane Skeleton and Synthesis of Two Energetic Derivatives

The construction of an all-bridge-oxygenated (hetero)adamantane skeleton is a long-standing challenge. Herein, an all-bridge carbon-oxidized 2-azaadamantane skeleton, 6,9,10-trimethoxy-2-azaadamantane-4,8-diol, was constructed via an eight-step synthetic route from 9-hydroxybicyclo[3.3.1]nonane-2,6-dione with an overall yield of 45%. The obtained skeleton was derived into two novel high-performance energetic compounds. Among them, 2,9,9,10,10-pentanitro-2-azaadamantane-4,6,8-triyl trinitrate is the first example that possesses eight explosophoric groups on the adamantane skeleton.