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Efficient halogenation of unsaturated organoaluminum compounds with sulfonyl halides

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Abstract

Alkenylalumanes prepared by carbo-or cycloalumination of substituted acetylenes reacted with an equivalent amount of sulfonyl halide (MsCl, TsCl, PhSO2Cl, MsBr) in methylene chloride or hexane at room temperature to produce alkenyl halides in high yields. Electron-donor solvents such as diethyl ether or tetrahydrofuran inhibited the halogenation process. β-Substituted vinylalumanes generated by hydroalumination of substituted acetylenes failed to react with sulfonyl halides.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Bashkortostan, Russia

    I. R. Ramazanov, R. N. Kadikova & U. M. Dzhemilev

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  1. I. R. Ramazanov
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  2. R. N. Kadikova
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  3. U. M. Dzhemilev
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Correspondence to I. R. Ramazanov.

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Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on her jubilee

Original Russian Text © I.R. Ramazanov, R.N. Kadikova, U. M. Dzhemilev, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 3, pp. 335–340.

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Ramazanov, I.R., Kadikova, R.N. & Dzhemilev, U.M. Efficient halogenation of unsaturated organoaluminum compounds with sulfonyl halides. Russ J Org Chem 49, 321–326 (2013). https://doi.org/10.1134/S1070428013030020

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  • DOI: https://doi.org/10.1134/S1070428013030020

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