(E)-9,10-Dihydro-9-methyl-9-nitro-10-(trinitromethyl)anthracene

Abstract

The title compound, C16H12N4O8, was prepared by the photochemical reaction of 9‐methyl­anthracene and tetra­nitro­methane in dichloromethane. Intermolecula face‐to‐face π–π stacking inter­actions are present along the a axis.

10,10′-Dinitro-10,10′-(propane-1,3-diyl)di-10H-anthracen-9-one

“…In this paper we report the crystal structure of the title compound, (I), the decomposition product of (E,E)-1,3bis[9,10-dihydro-9-nitro-10-(trinitromethyl)-9-anthryl]prop ane. The bond lengths and angles in the two anthracene ring systems (Table 1) are in agreement with each other, as well as with those of related compounds (Brinkmann et al, 1970;Rabideau, 1978;Dalling et al, 1981;Arslan et al, 2005).…”

“…The title compound was obtained as the decomposition product of (E,E)-1,3-bis[9,10-dihydro-9-nitro-10-(trinitromethyl)-9-anthryl]-propane, which was synthesized by irradiation with visual light of a solution containing 20 mg (0.050 mmol) of 1,3-bis(9-anthryl)propane, 325 mg (1.67 mmol) of TNM, 45 ml of pentane, and 5 ml of CCl 4 as described by Arslan et al (2005). A 450 W Hanovia medium-pressure mercury lamp with a 500 nm sharp cut-off filter was used as a light source.…”

“…In general, addition of TNM to 9-alkyl-substituted anthracenes proceeds at the 9-and 10-positions, with the nitro group bonding to atom C9, bearing the alkyl group, and the trinitromethyl group being attached to the sterically less hindered unsubstituted C10 center. We have already reported the structure of the product of such a process, (E)-9,10-dihydro-9-methyl-9-nitro-10-(trinitromethyl)anthracene (Arslan et al, 2005). One interesting feature of these trinitromethyl-substituted anthracene derivatives is that they contain the highly labile C-C(NO 2 ) 3 bond and, therefore, when passed through silica gel or an alumina column, easily decompose to form the corresponding anthrone derivatives.…”

9,10,12,13,14,15-Hexahydro-11H-9,10[1′,3′]cyclopentanthracene in two modifications

“…Calculation gives this angle as 56.0°by RHF and 55.1°by the higher-level MP2. Note specifically that the C4a-C9a bond, which lies below the methylene (C15) carbon, is nearly the same length [33][34][35][36], consistent with the distances found here. The bond distances of methylene carbons in strained rings such as cyclopropane (1.510 Å [37]) are slightly compressed relative to those of unstrained tetrahedral methylene carbons, which are expected to be near 1.54 Å such as in adamantine [38].…”

(E,E)-1,3-Bis[9,10-dihydro-9-nitro-10-(trinitromethyl)-9-anthryl]propane

“…Nitration through the irradiation of the charge-transfer complexes formed between aromatic compounds and tetranitromethane (TNM) offers an alternative route to the use of concentrated acids (Kochi, 1991;Butts et al, 1996;Cox, 1998;Lehnig & Schü rmann, 1998). We have already reported the crystal structure of (E)-9,10dihydro-9-methyl-9-nitro-10-(trinitromethyl)anthracene as the product of the photoreaction between 9-methylanthracene and TNM (Arslan et al, 2005). In the present paper, we report the crystal structure of the title compound, (I), which is a product of the photoreaction between 1,3-di-9-anthrylpropane, a dimeric analogue to 9-methylanthracene, with TNM.…”