Synthesis of 1,3,3-trinitroazetidine

Details Synthesis of 1,3,3-trinitroazetidine Synthesis of 1,3,3-trinitroazetidine

1993-06-07

1994-08-09

Ramsuer, Robert W.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20504

Patent

active

053367847

ABSTRACT:
A process of preparing 1,3,3-trinitroazetidine including forming a 5-hydroxymethyl-5-nitro-1-alkyltetrahydro-1,3-oxazine, e.g., reacting a 1,3,5-trialkyl hexahydrotriazine and tris(hydroxymethyl)nitromethane, ring opening said 5-hydroxymethyl-5-nitro-1-alkyltetrahydro-1,3-oxazine to form a 3-alkylamino-2-hydroxymethyl-2-nitro-1-propanol salt, ring closing said 3-alkylamino-2-hydroxymethyl-2-nitro-1-propanol salt to form a 3-hydroxymethyl-3-nitro-1-alkylazetidine salt, nitrating said 3-hydroxymethyl-3-nitro-1-alkylazetidine salt to form a 1-alkyl-3,3-dinitroazetidine, and converting said 1-alkyl-3,3-dinitroazetidine into 1,3,3-trinitroazetidine is disclosed.

REFERENCES:
Piotrowska et al., "Reaction of 2,2-dinitropropane-1,3-diol with 1,3,5-trialkylhexhydro-s-triazines" J. Org. Chem., vol. XIX, No. 6-7, pp. 359-362 (1971).
Piotrowska et al., "5-Bromo-5-Nitrotetrahydro-1,3-Oxazines"* , 5-Bromo-5-Nitrotetrahydro-1,3-Oksazyny, Roczniki Chemii, Ann. Socl. Chim. Polonorum 47, 193 (1973).
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Sammes et al., "Preparation of Azetidines from 1,3-Aminopropanols" J. Chem. Soc. Perkin Trans. I pp. 2415-2419 (1984).
Sammes et al., "On the Synthesis of Azetidines from 3-Hydroxycypropylamines" J. Chem. Soc., Commun., (1983) pp. 682-684.
Carlock et al., "A Mild Quantitative Method for the Synthesis of a Variety of Heterocyclic Systems" Tetrahedron Ltrs. No. 52, pp. 5153-5156 (1978).
Garver et al., "Catalyzed Oxidative Nitration of Nitronate Salts.sup.1 " J. Org. Chem., 50, pp. 1699-1703 (1985).
Archibald, T. G. et al., "Synthesis and X-Ray Crystal Structure of 1,3,3-Trinitroazetidine" J. Org. Chem. 1990, 55, 2920-2924.
Hiskey, M. et al., "Synthesis of 3,3-Dimtroazetidine from 1-t-Butyl-3,3-dinitroazetidine", J. Het. Chem. 1992, 29 No. 7, 1855-1856.

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