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2133004 
Journal Article 
Polycyclic fluoranthene hydrocarbons: 2. A new general synthesis 
Cho, BP; Harvey, RG 
1987 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
BIOSIS/88/10369 
52 
26 
5668-5678 
eng 
BIOSIS COPYRIGHT: BIOL ABS. A novel and efficient synthetic approach to polycyclic fluoranthene hydrocarbons is described. The method entails fusion of an indeno ring to an appropriate alternant hydrocarbon via reaction of its aryllithium derivative with cyclohexene oxide, followed by oxidation, cyclodehydration, and aromatization. Cyclization of the cyclohexanone and cyclohexanol derivatives of the polycyclic aromatic ring systems studied proceeds with high regioselectivity, and the direction of ring clousure is predictab by molecular orbital methods. This synthetic approach provides a convenient general route to polyaromatic fluoranthene compounds, including potentially carcinogenic members of this class. Hydrocarbon synthesized by this method include benz(e)acephenanthrylene (1), indeno(1,2,3-cd)pyrene (2), indeno(1,2,3-hi)chrysene (3), benz(def)indeno(1,2,3-hi)chrysene (4), fluoreno-(3,2,1,9-defg)chrysene (5), dibenz(a,e)aceanthrylene (6), dibenz(aj)aceanthrylene (7), benz(a)aceanthrylene (8),