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

MA Hiskey, MD Coburn, MA Mitchell…

Index: Hiskey, Michael A.; Coburn, Michael D.; Mitchell, Michael A.; Benicewicz, Brian C. Journal of Heterocyclic Chemistry, 1992 , vol. 29, # 7 p. 1855 - 1856

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Citation Number: 45

Abstract

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.