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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
One-Step Realization of Skeleton Editing, gem-Dinitromethyl Functionalization, and Zwitterionization in a
Mingren Fan1, Xiu'e Jiang1, Ruihui Wang1
1School of Astronautics, Northwestern Polytechnical University, Xi'an, Shaanxi 710065, China.
Abstract:
The single-atom skeletal editing technology is an efficient method for constructing molecular skeletons, which has broad coverage in synthetic chemistry. However, its potential in the preparation of energetic heterocyclic molecules is grossly underexplored. In this work, an unexpected one-step reaction for the synthesis of novel energetic molecules was discovered which combines single-atom skeletal editing, gem-dinitromethyl functionalization, and zwitterionization in one step. The reaction demonstrates high efficiency while maintaining the characteristics of being mild and facile. The reaction mechanism was verified by experimental evidence and theoretical calculations. This reaction produces a novel energetic molecule (NPX-04) with good laser ignition performance, indicating its promise as a laser-sensitive energetic material.
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