Synthesis of 3,3-dinitroazetidine from 1-t-butyl-3,3-dinitroazetidine

✍ Scribed by Michael A. Hiskey; Michael D. Coburn; Michael A. Mitchell; Brian C. Benicewicz

• Book ID: 112130528
• Publisher: Journal of Heterocyclic Chemistry
• Year: 1992
• Tongue: English
• Weight: 98 KB
• Volume: 29
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570290730

✦ Synopsis

Abstract

Treatment of 1‐t‐butyl‐3,3‐dinitroazetidine (1) with benzyl chloroformate resulted in a novel elimination of isobutylene to yield equimolar amounts of 1‐(benzyloxycarbonyl)‐3,3‐dinitroazetidine (3) and 1‐t‐butyl‐3,3‐dinitroazetidine hydrochloride. The carbamate 3 was effectively cleaved by trifluoromethanesulfonic acid to yield 3,3‐dinitroazetidinium trifluoromethanesulfonate (4). Free 3,3‐dinitroazetidine (5) has also been isolated.