Nair, Vijay ; Kumar, Sasi ; Anilkumar, Gopinathan ; Anilkumar, G. ; Radhakrishnan, K. V. ; Somarajan Nair, J. ; Maliakal, Davis ; Sheela, K. C. ; Mathew, Bini ; Treesa, P. M. (1998) Novel cycloaddition reactions of o-benzoquinones and related chemistry Proceedings of the Indian Academy of Sciences - Chemical Sciences, 110 (6). pp. 507-516. ISSN 0253-4134
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Official URL: http://www.ias.ac.in/j_archive/chemsci/110/2/507-5...
Related URL: http://dx.doi.org/10.1007/BF02872577
Abstract
o-Benzoquinone is a unique conjugated 1,2-dione that can exhibit diverse cycloaddition modes, participating either as carbodiene, heterodiene, dienophile or heterodienophile. With electron-rich dienes, benzodioxins are formed in excellent yields. Pentafulvenes including 6-vinylfulvenes normally give rise to bicyclo [2.2.2] adducts. Exceptions are observed with cycloalkylfulvenes where the fulvenes undergo rearrangement to cyclopentadiene derivatives prior to cycloaddition, resulting in benzodioxins. o-Benzoquinones participate as dipolarophiles on treatment with nitrile oxides and carbonyl ylides yielding highly oxygenated novel spiro compounds. Triphenylphosphine catalyzed addition of DMAD to o-benzoquinones afforded another class of novel spirolactones. The bicyclo [2.2.] octene diones derived fromo-benzoquinones undergo a number of synthetically useful transformations.
Item Type: | Article |
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Source: | Copyright of this article belongs to Indian Academy of Sciences. |
Keywords: | O-Benzoquinones; Cycloaddition Reactions; Benzodioxins; Bicyclo [2; 2; 2]octene Diones |
ID Code: | 84123 |
Deposited On: | 24 Feb 2012 11:41 |
Last Modified: | 19 May 2016 00:41 |
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