Photoinduced C-Br homolysis of 2-bromobenzophenones and pschorr ring closure of 2-aroylaryl radicals to fluorenones

Narasimha Moorthy, Jarugu ; Samanta, Subhas (2007) Photoinduced C-Br homolysis of 2-bromobenzophenones and pschorr ring closure of 2-aroylaryl radicals to fluorenones Journal of Organic Chemistry, 72 (25). pp. 9786-9789. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo7017872

Related URL: http://dx.doi.org/10.1021/jo7017872

Abstract

A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl s-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl σ-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:60749
Deposited On:10 Sep 2011 11:40
Last Modified:10 Sep 2011 11:40

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