Mehta, Goverdhan ; Viswanath, M. Balaji ; Jemmis, Eluvathingal D. ; Sastry, G. Narahari (1994) An approach to functionalized cubanes. Regioselectivities and frontier molecular orbital analysis in the addition of dimethyl cyclobutadiene-1,2-dicarboxylate to quinones Journal of the Chemical Society, Perkin Transactions 2 (3). pp. 433-436. ISSN 0300-9580
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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1994...
Related URL: http://dx.doi.org/10.1039/P29940000433
Abstract
4 + 2 Cycloaddition between dimethyl cyclobutadiene-1,2-dicarboxylate and benzoquinone, 4, gives 6, 7 and 8 in the ratio 15:4:1. Similarly naphthoquinone, 5, furnishes 9, 10 and 11 in the ratio 11:1:2. Formation of symmetrical adducts is predominent in both cases, Irradiation of major adducts 6 and 9 results in a cascade of photorearrangements. Semiempirical AM1 calculations are used to rationalize the regioselectivities.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 29014 |
| Deposited On: | 18 Dec 2010 05:42 |
| Last Modified: | 18 Dec 2010 05:42 |
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