Chemistry of 1-Fluoro-2,3,4-triphenylcyclobutadiene Dimers

Choudhury, Angshuman R and Chopra, Deepak and Guru Row, Tayur N and Nagarajan, Kuppuswamy and Roberts, John D (2007) Chemistry of 1-Fluoro-2,3,4-triphenylcyclobutadiene Dimers. In: Journal of Organic Chemistry, 72 (25). pp. 9732-9735.

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Abstract

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.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemcial Society
Additional Information:	Copyright of this article belongs to American Chemcial Society.
Department/Centre:	Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited:	03 Jun 2008
Last Modified:	19 Sep 2010 04:45
URI:	http://eprints.iisc.ac.in/id/eprint/14160

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