Phenanthrene-4,5-dicarboxylic anhydride

Benzo[c]phenanthrene-5,6-dicarboxylic anhydride and 6//-bcnzo[tt7]pyrcnc-6-one have been found to form combustion effluents benzo[g/ ]fluoranthene and cyclo-penta[cJ]pyrene on thermolysis.53... 

Thiophen Analogues of Polycyclic Aromatic Hydrocarbons Analogues of Anthracene and Phenanthrene. - Keto-enol tautomerism in a naphtho- and several anthra-thiophen systems [such as (241) (242)] has been studied. The system (241) (242) was obtained via the Friedel-Crafts reaction of thiophen with naphthalene-2,3-dicarboxylic anhydride followed by ring-closure. A [c] -fused system was similarly obtained by starting from... 

Diphenylcyclobutene- dione benzene acetonitrile sun phenanthrene-9,10-dicarboxylic acid anhydride 24)... 

Ozonation of benzo[r,s,t]pentaphene (7) followed by oxidative workup led to benzo[r,s,t]pentaphene-5,8-dione (12) (14%), phthalic acid (13) (4%), p-terphenyl-2,2, 3, 2"-tetra-carboxylic acid-2, 3 -anhydride (14) (10%), and 2-(o-car-boxyphenyl)- ,10-phenanthrenedicarboxylic acid anhydride (15) (3%), with a 56% recovery of unreacted 7, Ozonation of pentaphene (11) led to a peroxidic mixture which on oxidative workup led to 2,2 -binaphthyl-3,3 -dicarboxalde-hyde (16) (16%), 2,2 -binaphthyl-3,3 -dicarboxylic acid (17) (16%), and 13 (2%), with a 28% recovery of unreacted 11. A comparison of the reactivity to ozone of carcinogenic polycyclic aromatics benzo c]phenanthrene (1), 7,12-di-methylbenz [a] anthracene (2), 3-methylcholanthrene (3), dibenz[si,]] - (4), and dibenzlsi, ]anthracene (5), benzo Si -pyrene (6) and 7, and the noncarcinogen 11, all determined in our laboratory, leads us to conclude that there is no simple, consistent correlation between carcinogenicity, K-and L-region additivity towards ozone and the Pullmans electronic theory of carcinogenesis. 

These results show that reduction of the multiple bonds takes place through trans-addition. By reduction of diphenylacetylene in dimethylformamide in the presence of carbon dioxide Wawzonek and Wearring [103] obtained diphenylfumaric acid, diphenylmaleic anhydride and meso-diphenylsuccinic acid in the proportions 2,5 1 7. If it is assumed that the meso acid is formed from fumaric acid, these results demonstrate the stereospecificity of the process, contrary to the assertions made by Wawzonek and Wearring [103], From phenanthrene in the presence of carbon dioxide they obtained trans- 9,10-dihydrophenanthrene-9,10-dicarboxylic acid. 

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