By Professor Gianfranco Cainelli, Professor Giuliana Cardillo (auth.)

Chromium oxidation, renowned and extensively explored in natural chemistry because the very starting of this technology, is a subject of present curiosity for the natural chemist as evidenced by way of the continual improvement of recent techni­ ques and methods suggested within the literature. Chromium oxidation is an easy method which are simply played within the laboratory and scaled up in besides. even though nearly each oxidizable natural sensible team may perhaps suffer chromium oxidation, an important fields of appli­ cation are the oxidation of alcohols, allylic and benzylic oxidation, oxidative degradation and oxidation of a few organometallic compounds. A excessive measure of selectivity is usually attainable by way of deciding on the main appropriate reagent between these numerous ones now to be had. This booklet takes account of some of the useful teams that endure oxidation and the whole literature as much as 1982. it's been written within the wish to aid the artificial natural chemist in his experimental paintings. For this function a couple of tables comprising yields and references were integrated; particular descriptions of usual strategies are supposed to express the experimental stipulations and the scope of the reactions. we want to thank Dr. Mario Orena for his worthy clinical and technical assistence and Prof. Bruno Camerino, who learn the complete manuscript and corrected a number of the blunders. Bologna, February 1984 Gianfranco Cainelli Giuliana Cardillo desk of Contents I. creation . . . . . . . . . . .

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Steroids, p. 507, New York, Reinhold Publ Corp. 1959 25. FIAT, Final Report nO 996 26. : Chern. Ber. 66, 1274 (1966) 27. : Mikrochemie ver. Mikrochem. Acta 33,51 (1978) 28. : Comprehensive Analytical Chemistry, Vol. 1B (ed. Wilson and Wilson), Amsterdam, Elsevier 1960 29. : Methoden der Organ. Chemie (Houben-Weil), Vol. II, p. 276, Stuttgart, Thieme 1953 30. Cfr. : Acta Acad. Scandinavica 6,682 (1952) 31. Tashinian, V. , Baker, M. , Koch, e. : Anal. Chern. 28,1304 (1956) 32. Westheimer, F. : Chern.

L(COOH Na2C1'207 H2O I Na2CI'207 H2O s I N Table 4 reports the most interesting results obtained. 2 1 at 250°C for 15-18 hrs. The green hydrated chromium oxide in the reaction mixture is separated by filtration and the filtrate acidified with hydrochloric acid. After the mixture has cooled overnight the precipitate is filtered, washed well with water, and air dried giving 240 to 256 g (87-93 %) of 2,3-naphthalenedicarboxylic acid. The selectivity of this procedure is indicated by the oxidation of 2-methylnaphthalene which is cleanly converted into 2-naphthoic acid, whereas use of most-other oxidants results in ring degradation and formation of a considerable amount of 2-methylnaphthoquinone [65, 67]: rOO( c=::~:.

Oxidation of Carbon-Hydrogen Bonds in high yields to polynuclear carboxylic acids. Selective conversion of hydrocarbons such as I-methylnaphthalene, 2,6-dimethylnaphthalene, 4methylphenanthrene, 3-methylnaphthalene, and 3-picoline to their aromatic or heterocyclic carboxylic acids in 80-85 % yield illustrates the utility of this method [65]: ~ ~ 00 0s lOr N .. N82 CI'2 07 H2O HOOC~ COOH Q6? N82C1'207 H2O COOH .. OCOOH .. [l(COOH Na2C1'207 H2O I Na2CI'207 H2O s I N Table 4 reports the most interesting results obtained.

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Chromium Oxidations in Organic Chemistry by Professor Gianfranco Cainelli, Professor Giuliana Cardillo
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