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Molecular structure and reactions of 1,1 '-bi(acenaphthen-1-ylidene)-2,2 '-dione

Mehta, Goverdhan and Sarma, PVVS and Uma, R and Pogodin, Sergey and Cohen, Shumal and Agranat, Israel (1999) Molecular structure and reactions of 1,1 '-bi(acenaphthen-1-ylidene)-2,2 '-dione. In: Perkin Transactions 1, 1 (13). pp. 1871-1876.

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The molecular structure of 1,1'-bi(acenaphthen-1-ylidene)-2,2'-dione 1, a potential building-block for the synthesis of fullerene fragments, has been investigated by X-ray crystallography and semi-empirical (AM1 and PM3) calculations. There is a good agreement between the calculated and crystal structure which is essentially planar and has E-configuration. In the solid state, molecules of 1 pack in an interesting manner as corrugated sheets sustained by a network of C-H ... O hydrogen bonds and resulting in the formation of tetrameric loops. While steric factors limit the reactivity of the carbonyl groups in 1, the ene double bond of the ene-dione moiety present in it exhibits propensity toward [4 + 2]-cycloadditions to furnish novel and highly compressed polycycles 8-10.

Item Type: Journal Article
Publication: Perkin Transactions 1
Publisher: Royal Society of Chemistry
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 Jun 2011 10:26
Last Modified: 30 Jun 2011 10:26
URI: http://eprints.iisc.ac.in/id/eprint/38679

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