Synthesis and Properties of Nitrocarbenes and Diazirinone

摘要

The area of high energy density materials continues to receive a great deal ofattention. This is due to the need to package more energy into a smaller volume. Highly symmetric compounds have high densities and the strain energy of highly strained compounds serves to increase their heat of formation and therefore lead to improved performance as propellants, explosives and fuels. This is not a new idea. Indeed, there is presently a large effort directed towards the preparation of energetic cubane derivatives. However, the synthesis of cubane derivatives has been a tremendous synthetic challenge and major breakthroughs in their preparation have been slow in coming. On the other hand, we have chosen to study less involved but still highly strained structures, namely cyclopropyl compounds. One class of such energetic compounds, the nitrocyclopropanes, has received minimal work. Over the past three years, we have developed efficient methodology for the formation and reactions of such systems based on nitrocarbene chemistry. This progress report details the preparation and reactions of some of these nitro compounds. A second area of research covered during the grant period was a computational study of a novel, high energy density compound diazirinone. In addition, our experimental attempts to prepare this compound are also included. (JES)