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Paracyclophanes. Part 58 [1]. On the Use of the Stilbene-Phenanthrene Photocyclization in 2.2]Paracyclophane Chemistry

Hopf H., Hucker J., Ernst L.

Polish Journal of Chemistry

2007

Vol. 81, nr 5-6

947-969

The application of the stilbenephenanthrene photocyclization to [2.2]paracyclophane chemistry has been investigated. For the model system 4-styryl[2.2]paracyclophane (2) to [2.2]phenanthrenoparacyclophane (3) the reaction allows the introduction of alkyl substituents in the 6-, 7-, 8- and 9-position of the phenanthrene moiety. However, when the substituent in the 9-position (bay area of phenanthrene nucleus) becomes too large, viz. tert-butyl, no ring closure is observed anymore. The side products of the process (ring cleavage products of the cyclophane core such as 9 and 10) have been characterized for the first time. Extension of the condensed deck is possible leading to PAH-phanes as demonstrated by the preparation of the chrysenophanes 45 and 60; the cyclization to novel helicenophanes such as 50 also takes place without difficulties. In the case of 1,2-di- (4-[2.2]paracyclophanyl)ethene (63) the triply-layered hydrocarbon 65 is produced on irradiation in small amounts.