Pentaerythritol Tetranitrate → Cyclonite mixture with pentaerythritol tetranitrate

Participants

Reaction Steps

The photoreaction of DHA2 with either RDX or PETN yielded the nitrated product 31; however, compound 33 was also isolated from the reaction mixture. The yield of 33 was found to be somewhat dependent on the concentration of DHA2, with a higher amount of 33 over 31 observed in dilute solutions. The yield of 33 was also higher relative to that of 31 when the photolysis of DHA2 and RDX/PETN was conducted in slightly wet acetonitrile. Compounds 31 and 33 were generally isolated in 80% combined yield after flash column chromatography of the photoreactions between DHA2 and either RDX or PETN. Furthermore, DHA6 was confirmed to produce 32 and 34 (by GC-MS analysis) upon photolysis in the presence of RDX/PETN. Without wishing to be bound by theory, compounds 33 and 34 may have been formed as a result of either H. or hydride abstraction reactions between DHA2 or DHA6 and the photodegradation products of RDX and PETN. GC-MS analyses of the photoreactions between the remaining DHAs (DHA3, DHA7, DHA9, DHA10-17) and either RDX or PETN similarly revealed the formation of mono-nitrated derivatives of the respective DHAs.

Provenance & Evidence