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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Photochemical Nitration by Tetranitromethane. XVII. The Regiochemistry of Adduct Formation in the Photochemical Reaction of 1-Methylnaphthalene and Tetranitromethane

JL Calvert, L Eberson, MP Hartshorn, n Maclaga and WT Robinson

Australian Journal of Chemistry 47(8) 1591 - 1604
Published: 1994

Abstract

Photolysis of the 1-methylnaphthalene/tetranitromethane charge-transfer complex yields the triad of 1-methylnaphthalene radical cation, nitrogen dioxide and trinitromethanide ion. Recombination of this triad gives predominantly 4-methyl-t-2-nitro-r-1-trinitromethyl-1,2- dihydronaphthalene (1), the epimeric 1-methyl-1-nitro-4-trinitromethyl-1,4-dihydronaphtha-lenes (2) and (3), 8-methyl-c-4-trinitromethyl-1,4-dihydronaphthalen-r-l-ol (4), nitro cyclo -adduct (5), 8-methyl-c-4-trinitromethyl-1,4-dihydronaphthalen-r-l-ol (6), hydroxy cyclo-adduct (7) and 4-methyl-t-1-trinitromethyl-1,2-dihydronaphthalen-r-2-ol (8). Adducts (1)- (3), (5), (7) and (8) are formed by attack of the trinitromethanide ion at C4 of the 1-methylnaphthalene radical cation, while adducts (4) and (6) are formed by corresponding attack at C5. Adduct (1) undergoes thermal cycloaddition to give the nitro cycloadduct (5) and it is assumed that the hydroxy cycloadduct (7) is formed in analogous manner from 4-methyl-t-1-trinitromethyl-1,2-dihydronaphthalen-r-2-ol (8). X-Ray crystal structure determinations are reported for adducts (1), (3)-(5) and (7).

https://doi.org/10.1071/CH9941591

© CSIRO 1994

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