Improved synthesis of an energetic material,1,3,3-trinitroazetidine exploiting 2-iodoxy benzoic acid (IBX) as an oxidising agent

摘要

Tetrahydropyranyl protected l,3-dihalo-2-propanol reacts with p-toluene sulfonamide in the presence of K_2CO_3 to give corresponding N-p-tosyl-3-azetidinol.Deprotection and oxidation with iodoxy benzoic acid followed by oximation of N-p-tosyl-3-azetidinone readily affords the corresponding azetidine oxime in almost quantitative yield.The subsequent oxidative nitrolysis of oxime gives 1,3,3-trinitroazetidine (TNAZ) through a new sequence of reactions with excellent purity ( > 99% ) and moderate yield (40% ).