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Title: Synthesis of 1,3,3-trinitroazetidine

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.

Inventors:
 [1];  [1]
  1. Los Alamos, NM
Issue Date:
Research Org.:
Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
OSTI Identifier:
869438
Patent Number(s):
5336784
Assignee:
Regents of University of California (Oakland, CA)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
DOE Contract Number:  
W-7405-ENG-36
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
synthesis; 3-trinitroazetidine; process; preparing; including; forming; 5-hydroxymethyl-5-nitro-1-alkyltetrahydro-1; 3-oxazine; reacting; 5-trialkyl; hexahydrotriazine; tris; hydroxymethyl; nitromethane; form; 3-alkylamino-2-hydroxymethyl-2-nitro-1-propanol; salt; closing; 3-hydroxymethyl-3-nitro-1-alkylazetidine; nitrating; 1-alkyl-3; 3-dinitroazetidine; converting; disclosed; including forming; /999/

Citation Formats

Hiskey, Michael A, and Coburn, Michael D. Synthesis of 1,3,3-trinitroazetidine. United States: N. p., 1994. Web.
Hiskey, Michael A, & Coburn, Michael D. Synthesis of 1,3,3-trinitroazetidine. United States.
Hiskey, Michael A, and Coburn, Michael D. Sat . "Synthesis of 1,3,3-trinitroazetidine". United States. https://www.osti.gov/servlets/purl/869438.
@article{osti_869438,
title = {Synthesis of 1,3,3-trinitroazetidine},
author = {Hiskey, Michael A and Coburn, Michael D},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1994},
month = {1}
}

Works referenced in this record:

Preparation of azetidines from 1,3-aminopropanols
journal, January 1984


Synthesis of 3,3-dinitroazetidine from 1- t -butyl-3,3-dinitroazetidine
journal, December 1992


Stereospecific cyclization of β-hydroxy aryl amides to β-lactams
journal, November 1984


Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine
journal, April 1990


On the synthesis of azetidines from 3-hydroxypropylamines
journal, January 1983


Catalyzed Oxidative Nitration of Nitronate Salts
journal, May 1985


A mild quamtitative method for the synthesis of a variety of heterocyclic systems
journal, January 1978