@article { ISI:000234124500008, title = {Improved synthesis of an energetic material, 1,3,3-trinitroazetidine (TNAZ) exploiting 2-iodoxy benzoic acid (IBX) as an oxidising agent}, journal = {Indian Journal of Chemistry Section B - Organic Chemistry including Medicinal Chemistry}, volume = {44}, number = {12}, year = {2005}, month = {DEC}, pages = {2560-2563}, publisher = {NATL INST SCIENCE COMMUNICATION}, type = {Article}, address = {DR K S KRISHNAN MARG, NEW DELHI 110 012, INDIA}, abstract = {

Tetrahydropyranyl protected 1,3-dihalo-2-propanol reacts with p-toluene sulfonamide in the presence of K2CO3 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\%).

}, keywords = {2-iodoxy benzoic acid, insensiive munitions, oxidative nitrolysis, oximination, strained ring, synthesis, trinitroazetidine}, issn = {0376-4699}, author = {Singh, A and Sikder, N and Sikder, AK} }