NEW METHOD FOR THE GENERATION AND TRAPPING OF 1-AZABICYCLO[1.1.0]BUTANE - APPLICATION TO THE SYNTHESIS OF 1,3-DINITROAZETIDINE

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