Chemistry of 1-fluoro-2,3,4-triphenylcyclobutadiene dimers

Choudhury, Angshuman R. ; Chopra, Deepak ; Guru Row, Tayur N. ; Nagarajan, Kuppuswamy ; Roberts, John D. (2007) Chemistry of 1-fluoro-2,3,4-triphenylcyclobutadiene dimers Journal of Organic Chemistry, 72 (25). pp. 9732-9735. ISSN 0022-3263

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The reaction of 2,4-dichloro-1,1-difluoro-3-phenyl-2-cyclobutene 1 with excess phenyllithium and subsequent transformations of the products have been reinvestigated. The phenyllithium reaction appears to proceed through the intermediacy of a fluorotriphenylcyclobutadiene 2 to produce a well-characterized dimeric trans-hexaphenyldifluorotricyclooctadiene 3a. Subsequent transformations of 3a gave a pentaphenyldihydrodifluoropentalene 4, which on acid hydrolysis formed a pentaphenyldihydropentalenone 5. When 3a was photolyzed in benzene, after purification, it afforded 6, an isomer of 5, probably by way of 7, an isomer of 4. Thermolysis of 3a also provided, in low yield, a substance believed to be a pentaphenylfluorophenanthrene 8. Along with isolation of 3a, and probably arising from a different isomer of the 3 family, was a pentaphenylfluorophenanthrene 9, which was suspected of being an isomer of 8. Single-crystal X-ray studies were used to derive structures for 4, 5, 6, and 9. Formation of the unusual and intriguing transformation products has at least been rationalized.

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Source:Copyright of this article belongs to American Chemical Society.
ID Code:33485
Deposited On:21 Mar 2011 14:30
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