Synthesis of 3,3-dinitroazetidine

Details Synthesis of 3,3-dinitroazetidine Synthesis of 3,3-dinitroazetidine

1993-03-29

1995-03-07

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20504

Patent

active

053959450

ABSTRACT:
The compound, 3,3-dinitroazetidine, and a process of preparing 3,3-dinitroazetidine including reacting a mixture of 1-tertiary-butyl-3,3-dinitroazetidine and benzyl chloroformate to form 1-(benzyloxycarbonyl)-3,3-dinitroazetidine, reacting the 1-(benzyloxycarbonyl)-3,3-dinitroazetidine and trifluoromethanesulfonic acid to form 3,3-dinitroazetidinium trifluoromethanesulfonate, and neutralizing the 3,3-dinitroazetidinium trifluoromethanesulfonate with a base to form 3,3-dinitroazetidine are provided. Salts of the 3,3-dinitroazetidine and preparation of such salts are also disclosed.

REFERENCES:
Hiskey et al., "Synthesis of 3,3-Dinitroazetidine from 1-t-Butyl-3,3-dinitroazetidine," J. Heterocyclic Chem., 29, vol. 29, pp. 1855-1856 (1992).
Archibald et al., "Synthesis and X-ray Crystal Structure of 1,3,3-Trinitroazetidine," J. Org. Chem., vol. 55, No. 9, pp. 2920-2924 (1990).
Yajima et al., "Trifluoromethanesulfphonic Acid, as a Deprotecting Reagent in Peptide Chemistry," J.C.S. Chem. Comm. pp. 107-108 (1974).
Hobson et al., "Cleavage of Tertiary Bases with Phenyl Chloroformate: The Reconversion of 21-Deoxyajmaline into Ajmaline," J. Chem. Soc. (C), pp. 2015-2017 (1967).
Glaser et al., "Stickstoff-Verbindungen II," (1957) p. 142.
Piotrowska et al., "Reactions of Nitroparaffins. Part XCVII* Novel Features of the Reaction of 2,2-Dinitropropanediol-1,3 with Primary Amines," Rocznike Chemii Ann. Soc. Chem. Polonorum 45, pp. 2107-2111 (1971).

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