- On the oxidation of 3-ethylpentane under GifIV and Gif-orsay conditions
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The oxidation of 3-ethylpentane under GifIV (and GoAggII) conditions affords, as major product, 3-acetylpentane and not diethylketone as previously reported. The discrepancy is explained by radical chain autoxidation in presence of a weak tertiary C - H bond.
- Barton, Derek H. R.,Doller, Dario,Ozbalik, Nubar,Balavoine, Gilbert,Gref, Aurore,Boivin, Jean
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- FUNCTIONALISATION OF SATURATED HYDROCARBONS. Part X. A COMPARATIVE STUDY OF CHEMICAL AND ELECTROCHEMICAL PROCESSES (GIF AND GIF-ORSAY SYSTEMS) IN PYRIDINE, IN ACETONE AND IN PYRIDINE-CO-SOLVENT MIXTURES
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Six saturated hydrocarbons (cyclohexane, 3-ethylpentane, methylcyclopentane, cis- and trans-decalin and adamantane) were oxidised by the Gif system (iron catalyst, oxygen, zinc, carboxylic acid) and its electrochemical equivalent (Gif-Orsay system).Results obtained using various solvents (pyridine, acetone, pyridine-acetone mixtures) were similar for both systems.Total or partial replacement of pyridine with acetone affects the selectivity for secondary positions and lowers the ketone/secondary alcohol ratio.The formation of the same ratio of cis- and trans-decal-9-ol from both cis- and trans-decalin clearly demonstrates that tertiary alcohols result from a mechanism essentially radical in nature.
- Belavoine, Gilbert,Barton, Derek H. R.,Boivin, Jean,Gref, Aurore,Coupanec, Pascale Le,et al.
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p. 1091 - 1106
(2007/10/02)
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- Stereochemistry of the Platinum Catalyzed Hydroformylation of Olefins
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The deuterioformylation of (Z)- or (E)-2-butene catalyzed by Pt(SnCl3)Cl gives predominantly erythro- or threo-1,3-2-2-methylbutanal respectively.Hence, hydroformylation by this catalytic system must take place with cis-stereochemistry.
- Haelg, Paul,Consiglio, Giambattista,Pino, Piero
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p. 1865 - 1869
(2007/10/02)
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