Revisit of the Dessy?White Intramolecular Acetylene?Acetylene [2 + 2] Cycloadditions
Resource
The Journal of Organic Chemistry 71 (22): 8417-8423
Journal
The Journal of Organic Chemistry
Journal Volume
71
Journal Issue
22
Pages
8417-8423
Date Issued
2006
Date
2006
Author(s)
Abstract
In this experiment, a series of thermal reactions of 4,4'-disubstituted 2,2'-bis(phenylethynyl)biphenyls with 2,3,4,5-tetraphenylcyclopenta-2,4-dienone were carried out under neat conditions and in diphenyl ether at temperatures between 260 and 270 degrees C to give rise to 9,10,11,12,13,14-hexaphenylcycloocta[l]phenanthrenes as the adducts in 12-23% yields. We traced these results to the intramolecular [2 + 2] thermal cyclization of 2,2'-bis(phenylethynyl)biphenyls to form 1,2-diphenylcyclobuta[l]phenanthrenes, which were further trapped as bridged-ketone Diels-Alder adducts, followed by thermal decarbonylative ring opening, which gave rise to the products.
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Type
journal article
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