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The electronic factor in Bergman cyclization

Pramanik, A and Kalyanaraman, P and Chandrasekhar, J (1997) The electronic factor in Bergman cyclization. In: Current science, 73 (6). pp. 527-528.

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Through-bond interactions in 1,4-dehydrobenzene preferentially stabilize the out-of-phase combination of the radical hydrids, The resultant splitting between the frontier orbitals is crucial in making Bergman cyclization a symmetry-allowed process. Orbital symmetry also inhibits the radical centers from forming a C-C bond, enabling the biradical to survive as a local minimum capable of intermolecular hydrogen abstraction, Both these factors, which are important in the design of DNA cleaving molecules, are confirmed through calculations on biradicals formed from diynes in which through-bond interactions stabilize the in-phase combination of hybrids at the radical centers.

Item Type: Journal Article
Publication: Current science
Publisher: Indian academy of sciences
Additional Information: Copyright for this article belongs to Indian academy of sciences.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 22 Jan 2010 07:06
Last Modified: 19 Sep 2010 05:51
URI: http://eprints.iisc.ac.in/id/eprint/24707

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