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

TitleImproved synthesis of an energetic material, 1,3,3-trinitroazetidine (TNAZ) exploiting 2-iodoxy benzoic acid (IBX) as an oxidising agent
Publication TypeJournal Article
Year of Publication2005
AuthorsSingh, A, Sikder, N, Sikder, AK
JournalIndian Journal of Chemistry Section B - Organic Chemistry including Medicinal Chemistry
Volume44
Issue12
Pagination2560-2563
Date PublishedDEC
Type of ArticleArticle
ISSN0376-4699
Keywords2-iodoxy benzoic acid, insensiive munitions, oxidative nitrolysis, oximination, strained ring, synthesis, trinitroazetidine
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%).

Type of Journal (Indian or Foreign)

Indian

Impact Factor (IF)0.471
Divison category: 
Biochemical Sciences