Sajimon, Meledathu C. ; Ramaiah, Danaboyina ; Kumar, S. Ajaya ; Rath, Nigam P. ; George, Manapurathu V. (2000) Substituent effects on regioselectivity in the photorearrangement of a few naphthobarrelenes Tetrahedron, 56 (30). pp. 5421-5428. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(00)00450-6
Abstract
The photorearrangement of a few 9,10-disubstituted-naphthobarrelenes to the corresponding naphthosemibullvalenes has been examined. It was observed that the regioselectivity in these photoisomerizations depends on the relative stabilities of the diradical intermediates. AM1 semi-empirical calculations are in support of this view. Thermal transformation of the naphthosemibullvalenes gave the corresponding water added naphthopentalenofurans, in nearly quantitative yields.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Di-π-methane Rearrangement; Naphthobarrelenes; Naphthosemi-bullvalenes; Regioselectivity |
| ID Code: | 12415 |
| Deposited On: | 10 Nov 2010 06:25 |
| Last Modified: | 31 May 2011 10:30 |
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