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Photochemical reaction of 9-nitro-substituted anthracene-like molecules 9-methyl-10-nitroanthracene and 12-methyl-7-nitrobenz[a]anthracene ☆

Paper ID Volume ID Publish Year Pages File Format Full-Text
28381 44072 2009 6 PDF Available
Title
Photochemical reaction of 9-nitro-substituted anthracene-like molecules 9-methyl-10-nitroanthracene and 12-methyl-7-nitrobenz[a]anthracene ☆
Abstract

Photolysis of 9-methyl-10-nitroanthracene in chloroform or methanol produces mainly two products 9-methyl-9-nitrosoanthracen-10-one and 9,10-anthraquinone in about 4:1 ratio under ambient air. The formation of 9-methyl-9-nitrosoanthracen-10-one confirms the proposed excited state rearrangement reaction of the nitro group peri to two hydrogens and perpendicular to the aromatic rings. The nitro group rearranges to a nitrite, followed by breaking of the N–O bond producing NO radical. The NO radical further forms a bond with the carbon on the opposite site of the benzene ring through radical recombination. Photolysis of 12-methyl-7-nitrobenz[a]anthracene produced several nitroso ketone-like compounds which further convert to an aldehyde. Photolysis of the desmethyl nitro compounds, 9-nitroanthracene and 7-nitrobenz[a]anthracene, produced the respective quinones.

Keywords
Photoreaction; 9-Methyl-10-nitroanthracene; 7-Nitrobenz[a]anthracene, 12-Methyl-7-nitrobenz[a]anthracene; Nitro-rearrangement
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Photochemical reaction of 9-nitro-substituted anthracene-like molecules 9-methyl-10-nitroanthracene and 12-methyl-7-nitrobenz[a]anthracene ☆
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 201, Issue 1, 1 January 2009, Pages 39–44
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Price was $35.95
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Price after discount Only $4.95
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