Photochemie aromatischer Nitroverbindungen, XVIII. Photolyse von 2,6‐Di‐ tert ‐butyl‐1‐nitronaphthalin

Abstract

Photochemistry of Aromatic Nitro Compounds, XVIII. – Photolysis of 2,6‐Di‐tert‐bytl‐1‐nitronaphthalene While o‐nitro‐tert‐butylbenzenes 1 generally undergo a light‐induced cyclization to 3H‐indole 1‐oxides 4 or products derived therefrom, the benzohomologous 2,6‐di‐tert‐butyl‐2‐nitro‐naphthalene (5) upon irradiation exclusively forms the binaphthylidene quinone 10; the 2‐tert‐butyl group remains unaffected during the photolysis.

Mapping the Triplet Potential Energy Surface of 1-Methyl-8-nitronaphthalene

“…These chemicals are among the most abundant aromatic compounds found in atmosphere . Gas-phase photolysis resulting in the formation of oxygenated compounds, such as quinones, is considered to be the major degradation pathway for these compounds. − Analogous products were detected upon photodecomposition of 2-substituted-1-nitronaphthalenes in solution. ,, These results are in clear contrast with early observations indicating that 1-nitronaphthalene (1NN) shows no detectable phototransformation in alcohol solution . It has to be pointed out that 1NN derivatives with a methyl group in the peri - or ortho -position were found to degrade upon photoirradiation much faster than 1NN and other isomeric methylnitronaphthalenes.…”