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An Oxidation Induced by Potassium Metal : Studies on the Anionic Cyclodehydrogenation of 1,1 `-Binaphthyl to Perylene

Rickhaus, Michel and Belanger, Anthony P. and Wegner, Hermann A. and Scott, Lawrence T.. (2010) An Oxidation Induced by Potassium Metal : Studies on the Anionic Cyclodehydrogenation of 1,1 `-Binaphthyl to Perylene. The journal of organic chemistry, Vol. 75, H. 21. pp. 7358-7364.

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Official URL: http://edoc.unibas.ch/dok/A5841480

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Abstract

Oxidative cyclization of 1, 1 `-binaphthyl (1) to perylene (2) can be achieved in essentially quantitative yield by the action of three or more equivalents of potassium metal in hot tetrahydrofuran. An overall reaction mechanism is proposed that accounts for all of the experimental observations reported by previous investigators and those from the present studies. The trans-6a,6b-dihydroperylene dianion (6(2-)) is believed lobe the pivotal intermediate from which H-2, is lost. A radical chain reaction involving free hydrogen atoms (H-center dot) in the two-step propagation cycle is proposed to explain the formation of H-2 from 6(2-). Anionic cyclodehydrogenations of this sort are complementary to those performed under strongly acidic/oxidizing conditions, photochemically, or thermally (flash vacuum pyrolysis), and a better understanding of how they occur, together with the optimized synthetic protocol reported here, should encourage their wider use in organic synthesis.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Synthese (Wegner)
UniBasel Contributors:Wegner, Hermann A. A.
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:American Chemical Society
ISSN:0022-3263
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:14 Sep 2012 07:20
Deposited On:14 Sep 2012 07:00

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