Réaction #1552071

Équation de réaction

PETN

RDX

9,9-dioctylfluorene

anisole

1,2-dimethoxybenzene

9,9-dioctylfluorene

9,9-dioctylfluorene

PETN

RDX

→

RDX

PETN

anisole

4-nitroanisole

Rendement 1.0%

Solvants

acetonitrile

THF

Conditions de réaction

Traitement

1. 1
   Autrethe scope of the photonitration reaction
2. 2
   Autrewas recovered in ca. 90% yield

Mode opératoire

To probe the scope of the photonitration reaction, the nitration of 9,9-dioctylfluorene, anisole and 1,2-dimethoxybenzene by RDX and PETN was investigated. Extended photolysis (5 h) of a mixture of 9,9-dioctylfluorene and either RDX or PETN in 1:1 acetonitrile:THF at either 254, 313, 334, or 356 nm did not generate any observable products and 9,9-dioctylfluorene was recovered in ca. 90% yield. Photolysis of anisole with RDX or PETN yielded only trace amounts of 4-nitroanisole (<1% GC yield) after 4 hours. Photolysis of 1,2-dimethoxybenzene with either RDX or PETN yielded 1,2-dimethoxy-4-nitrobenzene in only ca. 8% yield after 2 hours; moreover this reaction did not proceed cleanly and numerous polar photoproducts were observed. Based on this set of experiments, anilines were selected as candidates for potential indicators. To create fluorogenic indicators based on the facile nitration reaction between aromatic amines and the photofragmentation products of RDX and PETN, 9,9-disubstituted 9,10-dihydroacridines (DHAs) were targeted as chemosensory.

Source