A new method for the synthesis of dibeneo[a,l]pyrene and various derivatives has been achieved through anThe key to the new approach is to use 1-arylbena[a]anthracenes as the The parent hydrocarbon and derivatives containing application of the Scholl reaction. precursors to the desired polycyclic aromatic compounds. alkyl, halogen, and alkyoxyl substituents have been prepared as well as the corresponding TNF adducts.
a solution of 3p-methoxy-17a-meth.ylandrost-5-en-17p-o115 (1.0 g.) in 95% ethanol (35 ml.) was added 5 7 , palladium-on-carbon (0.1 g.). The mixture was hydrogenated at atmospheric pressure and room temperat~re.1~ Hydrogen uptake was complete after 3 hr. and the catalyst was removed by filtration and washed with ethanol. The solvent was removed from the filtrate and (15) 11. N. Huffnian and J. u'. Sadler, J . Org. Chem.. 18, 924 (1953). the residue crystallized from 95% ethanol. This gave VI1 (0.8 g.), m.p. 178-179', and a second crop (0.15 g.), m.p. 176-178". Recrystallization from methanol-water atlorded an analytical sample, m.p. [180][181]
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