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

Mehta, Goverdhan ; Sarma, P. V. V. S. ; Uma, R. ; Pogodin, Sergey ; Cohen, Shumal ; Agranat, Israel (1999) Molecular structure and reactions of 1,1'-bi(acenaphthen-1-ylidene)-2,2'-dione Journal of the Chemical Society, Perkin Transactions 1 (13). pp. 1871-1876. ISSN 0300-922X

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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:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:29055
Deposited On:18 Dec 2010 05:39
Last Modified:17 May 2016 12:02

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