A highly effective ligand-bound ruthenium catalyst for chemoselective degradation of aromatic rings to carboxylic acids

Chakraborti, Asit K. ; Ghatak, Usha Ranjan (1985) A highly effective ligand-bound ruthenium catalyst for chemoselective degradation of aromatic rings to carboxylic acids Journal of the Chemical Society, Perkin Transactions 1 (12). pp. 2605-2609. ISSN 0300-922X

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Official URL: http://www.rsc.org/publishing/journals/article.asp...

Related URL: http://dx.doi.org/10.1039/P19850002605

Abstract

A highly effective oxidation catalyst, generated in situ by reaction of cis-(2,2-bipyridine)2RuCl2·2H2O with sodium metaperiodate mimics ruthenium tetraoxide in the chemoselective degradation of aromatic rings in the 2-aryltricyclo[3.2.1.02,7]octan-6-ones (5a,b) and (6a,b) and the aryl substituted bicyclo[3.2.1]octanones (9a,b), (10a,b), (11), and (12) to the keto monocarboxylic acids (7a), (8a), (13a), (14a), (15a), and (16a) respectively. Similar oxidation reaction of the 2β-benzyl- and 2β-phenethyl-cyclohexane-1,3-carbolactones (17)-(20) affords the corresponding γ-lactone acids (20a)-(23a), whilst the fused tetracyclic hydroaromatic ketones (29a,b), (30a,b), (31a-c), and (35a,b) provide their respective keto dicarboxylic acids (32a)-(36a) in excellent yields. The incorporation of a methoxy substitution in the aromatic ring considerably facilitates the oxidation reaction.

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