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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. Journal of Organic Chemistry, 72 (25). pp. 9732-9735. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20160624-132914470

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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:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/jo701900kDOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo701900kPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jo701900kPublisherSupporting Information
Additional Information:© 2007 American Chemical Society. Publication Date (Web): November 3, 2007. Dedicated to Professor S. Swaminathan on the occasion of his 81st birthday. T.N.G. acknowledges funding (DST 0361) from the Department of Science and Technology, Government of India. At the California Institute of Technology, the research was supported by the National Science Foundation through grants funded in 1956-60 and currently under Grant No. CHE-0104273.
Funders:
Funding AgencyGrant Number
Department of Science and Technology (India)DST 0361
NSFCHE-0104273
Record Number:CaltechAUTHORS:20160624-132914470
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160624-132914470
Official Citation:Chemistry of 1-Fluoro-2,3,4-triphenylcyclobutadiene Dimers Angshuman R. Choudhury, Deepak Chopra, Tayur N. Guru Row, Kuppuswamy Nagarajan, and, and John D. Roberts, The Journal of Organic Chemistry 2007 72 (25), 9732-9735 DOI: 10.1021/jo701900k
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:68663
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:26 Jun 2016 12:06
Last Modified:26 Jun 2016 12:06

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