engleski

New Method for the Generation and Trapping of 1-Azabicyclo[1.1.0]butane. Application to the Synthesis of 1, 1-Dinitroazetidine

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.

Azabicyclobutane; dinitroazetidine

nije evidentirano