New method for the generation and trapping of 1- azabicyclo[1.1.0]butane. Application to the synthesis of 1,3- dinitroazetidine

Article abstract of DOI:10.1080/00397919808004953

1-Azabicyclo[1.1.0]butane (1) has been prepared via a two-step, one-pot procedure that involves (i) reaction of a heptane solution of allylamine with N-chlorosuccinimide at 0 °C followed by (ii) codistillation of the product from basic solution along with heptane-octane. Compound 1 thereby obtained was extracted from the distillate by using cold aqueous NaNO₂. Subsequent treatment of the aqueous extract with cold concentrated aqueous HCl afforded N-nitroso-3-nitroazetidine (4) in 5.5% yield. Oxidation of 4 with 100% HNO₃ produced N,3-dinitroazetidine (5, 90%). This reaction sequence constitutes a formal synthesis of 1,3,3-trinitroazetidine (TNAZ), an important energetic material.

Full text of DOI:10.1080/00397919808004953

This article was downloaded by: [Moskow State Univ Bibliote]
On: 01 December 2013, At: 08:25
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number:
1072954 Registered office: Mortimer House, 37-41 Mortimer Street,
London W1T 3JH, UK
Synthetic Communications:
An International Journal
for Rapid Communication of
Synthetic Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
New Method for the
Generation and Trapping of
1-Azabicyclo[1.1.0]butane.
Application to the Synthesis
of 1,3-Dinitroazetidine
Romuald Bartnik a , Dariusz Cal a , Alan P.
Marchand b , Sulejman Alihodzic b & Arokiasamy
Devasagayaraj b
a Department of Organic & Applied Chemistry ,
University of Lodz , Narutowicza, 68, 90-136,
Lodz, Poland
b Department of Chemistry , University of North
Texas , Denton, Texas, 76203-5070
Published online: 16 Aug 2006.
To cite this article: Romuald Bartnik , Dariusz Cal , Alan P. Marchand , Sulejman
Alihodzic & Arokiasamy Devasagayaraj (1998) New Method for the Generation
and Trapping of 1-Azabicyclo[1.1.0]butane. Application to the Synthesis of
1,3-Dinitroazetidine, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 28:21, 3949-3954, DOI:
10.1080/00397919808004953
To link to this article: http://dx.doi.org/10.1080/00397919808004953
PLEASE SCROLL DOWN FOR ARTICLE

Taylor & Francis makes every effort to ensure the accuracy of all
the information (the “Content”) contained in the publications on our
platform. However, Taylor & Francis, our agents, and our licensors
make no representations or warranties whatsoever as to the accuracy,
completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of
the authors, and are not the views of or endorsed by Taylor & Francis.
The accuracy of the Content should not be relied upon and should be
independently verified with primary sources of information. Taylor and
Francis shall not be liable for any losses, actions, claims, proceedings,
demands, costs, expenses, damages, and other liabilities whatsoever
or howsoever caused arising directly or indirectly in connection with, in
relation to or arising out of the use of the Content.
This article may be used for research, teaching, and private study
purposes. Any substantial or systematic reproduction, redistribution,
reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden. Terms & Conditions of access
and use can be found at http://www.tandfonline.com/page/terms-and-
conditions