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

被引：13

作者：

Bartnik, R

Cal, D

Marchand, AP

Alihodzic, S

Devasagayaraj, A

机构：

[1] Univ Lodz, Dept Organ & Appl Chem, PL-90136 Lodz, Poland

[2] Univ N Texas, Dept Chem, Denton, TX 76203 USA

来源：

SYNTHETIC COMMUNICATIONS | 1998年 / 28卷 / 21期

关键词：

D O I：

10.1080/00397919808004953

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 degrees 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.

引用

页码：3949 / 3954

页数：6

共 11 条

[1]

BARTNIK R, 1994, POL J CHEM, V68, P1347

[2]

Bartnik R, 1997, SYNLETT, P1029

[3] NITRO-STEROIDS .2. A NEW ROUTE TO NITRO-STEROIDS [J].