- Reactions with Nitrosodisulfonate, 41. Oxidation of Some Enols, Enamines, and Alcohols
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4,6-Dimethyl-1,3-cyclohexanedione is oxidized by potassium nitrosodisulfonate to the vicinal triketone 1. 5-Phenyl- and 5,5-pentamethylene-1,3-cyclohexanedione react with the aldehyde, produced by the dehydrogenation of the alcohol of the solvent, instead with the oxidant to give 2a, b and 3a. 1,2-Indanedione forms the ketol 5a, 1,3-indanedione mainly bindone.The splitting of a carbon-carbon bond is observed in the case of 2-methyl-1,3-cyclohexanedione (-> 5,6-dioxo-n-heptanoic acid), 1,2-cyclohexanedione (-> adipic acid), and dibenzyl ketone (-> benzoic acid). 1,3-Cycloheptanedione does not react.Skatole is oxidized to 2-(formylamino)-5-hydroxyacetophenone, and the Fischer base with ring enlargement to the stereoisomeric quinoline derivatives 12a and b.
- Teuber, Hans-Joachim,Hohn, Juergen,Gholami, Abbas
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p. 1309 - 1319
(2007/10/02)
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