Preparation of 1-substituted-3,3-dinitroazetidines

Abstract
DNAZ (3,3-dinitroazetidine), 1, readily undergoes nucleophilic addition reactions with electron deficient haloaromatics, cyanogen bromide, S-methyl-N-nitroisothiourea and dichloroglyoxime to afford novel, energetic 1-substituted-3,3-dinitroazetidines. N-Nitrosation of DNAZ readily occurs, and Mannich condensations of DNAZ with poly-nitroalcohols are also described. The synthesis and properties of the energetic materials derived from these reactions will be discussed.