Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane

Vera S. Glukhacheva, Sergey G. Il’yasov, Elena O. Shestakova, Egor E. Zhukov, Dmitri S. Il’yasov, Anastasia A. Minakova, Ilia V. Eltsov, Andrey A. Nefedov, Alexander M. Genaev

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

Аннотация

Here, we report the study results of the nitration of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane (THAP) by different nitrating agents such as nitric acid, mixed nitric/sulfuric acids, nitric anhydride, and mixed concentrated nitric acid/acetic anhydride to furnish 3,7,10-trioxo-2-nitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane and 3,7,10-trioxo-2,8-dinitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane, whereas a lactam–lactim rearrangement was found to take place upon vigorous cooling to give 10-hydroxy-2,4,6,8,9,11-hexaazatricyclo[3.3.3.01,5]undec-9-ene-3,7-dione. The two competing reactions, lactam–lactim rearrangement, and nitration were found to take place. The acylation of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane was examined and the formation conditions of 2,6-di- and 2,6,9-triacetyl-substituted and 3,7,10-trioxo-2,4,6,8,9,11-hexaacetyl-2,4,6,8,9,11-hexaaza[3.3.3]propellane were established. The acetyl derivatives were found to be instable in an acidic medium and to undergo deacylation. The obtained findings correlate well with the quantum-chemical calculations.

Язык оригиналаанглийский
Номер статьи8320
ЖурналMaterials
Том15
Номер выпуска23
DOI
СостояниеОпубликовано - дек. 2022

Предметные области OECD FOS+WOS

  • 2.05 ТЕХНОЛОГИЯ МАТЕРИАЛОВ
  • 1.03 ФИЗИЧЕСКИЕ НАУКИ И АСТРОНОМИЯ

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