
%0 Journal Article
%A Butts, CP 
%A Eberson, L 
%A Fulton, KL 
%A Hartshorn, MP 
%A Robinson, WT 
%T Photochemical Nitration by Tetranitromethane. XXXII. Adduct Formation in the Photochemical Reaction of Phenanthrene and Tetranitromethane
%J Australian Journal of Chemistry
%D 1996/04/01
%V 49
%N 4
%P 469-473
%K 
%R https://doi.org/10.1071/CH9960469
%U https://www.publish.csiro.au/paper/CH9960469 
%X Photolysis of the phenanthrene/tetranitromethane charge-transfer complex yields the triad of phenanthrene radical cation, nitrogen dioxide, and trinitromethanide ion. Recombination of this triad in dichloromethane at 20&#176; gives 9-nitrophenanthrene (1), trans-10-trinitromethyl-9,10-dihydrophenanthren-9-yl nitrate (2a), trans-9-nitro-10-trinitromethyl-9,10-dihydrophenanthrene (2b), and trans-10-trinitromethyl-9,10-dihydrophenanthren-9-ol (2c). Adduct formation is partially suppressed when trifluoroacetic acid (0.7 M) is added to the dichloromethane solvent at 20&#176;, the major product identified being 9-nitrophenanthrene (1). At -20&#176; in dichloromethane, or in acetonitrile at 20&#176;, 10'-nitro-9,9',10,10'-tetrahydro-9,9'-biphenanthren-10-yl nitrate (3) is formed, apparently by reaction of nitrogen dioxide with phenanthrene. X-Ray crystal structure determinations are reported for adducts (2a,b). 
