Abstract
Base-catalyzed isomerization of recently reported hexaallylhexaazaisowurtzitane produced a new derivative, hexa(1-propenyl)hexaazaisowurtzitane (HPIW). Photooxygenation of this intermediate by singlet oxygen oxidized most of the 1-propenyl substituents to formyl substituents. The course of this reaction of singlet oxygen with HPIW involves peroxide intermediates, which may include relatively stable macrocyclic (tetroxocane) derivatives. The resulting nitrolyzable polyformylhexaazaisowurtzitane was found to be a promisingly efficient new precursor to CL-20 (in a single preliminary experiment without any process development). The new intermediate HPIW also underwent direct nitrolysis to form CL-20, though not as efficiently as its photooxygenation product did.
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