Ghatak, Usha R. ; Alam, Shaikh Khairul ; Chakraborti, Prabir C. ; Ranu, Brindaban C. (1976) Condensed cyclic and bridged-ring systems. Part IV. Stereochemically controlled synthesis of some endo-2-aryl-6-oxobicyclo[3.2.1]octanes and related compounds through intramolecular alkylations of γδ-unsaturated α'-diazomethyl ketones Journal of the Chemical Society, Perkin Transactions 1 (16). pp. 1669-1673. ISSN 0300-922X
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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1976...
Related URL: http://dx.doi.org/10.1039/P19760001669
Abstract
The 4-arylcyclohex-3-enecarboxylic acids (4a-d), prepared through a modified Diels-Alder reaction, have been converted via the corresponding diazomethyl ketones (5a-d) into cyclopropyl ketones (6a-d) and the 2-aryl-6-oxobicyclo[3.2.1]oct-2-ene derivatives (7a-d), by oxo-carbenoid addition and boron trifluoride-ether-catalysed cyclisation, respectively, in excellent yields. In addition to the unsaturated ketones (7a and c), the hydroxy-ketones (10a and c) were also obtained in the aqueous tetrafluoroboric acid-catalysed cyclisation of the diazoketones (5a and c). Catalytic reduction of the cyclopropyl ketones and the unsaturated ketones produced the endo-2-aryl-6-oxobicyclo[3.2.1]octane derivatives (8a-d) exclusively.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 28143 |
| Deposited On: | 14 Dec 2010 08:14 |
| Last Modified: | 02 Jun 2011 06:57 |
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