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Oxidative addition of trifluoromethanesulfonamide to cycloalkadienes

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Abstract

Reactions of trifluoromethanesulfonamide with cyclopentadiene, cyclohexa-1,3- and -1,4-dienes, cyclohepta-1,3,5-triene, and cycloocta-1,3-diene in the presence of t-BuOCl-NaI were studied. Trifluoromethanesulfonamide added at one double bond of cyclopentadiene and cyclohexa-1,3-diene in regio- and stereoselective fashion to give N-(5-iodocyclopent-2-en-1-yl)trifluoromethanesulfonamide and trans-N,N′-cyclohex-3-ene-1,2-diylbis(1,1,1-trifluoromethanesulfonamide), respectively. The reaction with cyclohexa-1,4-diene involved both isolated double bonds to produce N,N′-(2-chloro-5-iodocyclohexane-1,4-diyl)bis(1,1,1-trifluoromethanesulfonamide) which underwent halophilic reduction of the CHI group by the action of NaI and elimination of HCl, leading to N,N′-(cyclohex-2-ene-1,4-diyl)bis(1,1,1-trifluoromethanesulfonamide). Under analogous conditions, cyclohepta-1,3,5-triene was oxidized to benzaldehyde, while no reaction with trifluoromethanesulfonamide occurred.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. Yu. Moskalik, V. V. Astakhova & B. A. Shainyan

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  1. M. Yu. Moskalik
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  2. V. V. Astakhova
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  3. B. A. Shainyan
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Correspondence to M. Yu. Moskalik.

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Original Russian Text © M.Yu. Moskalik, V.V. Astakhova, B.A. Shainyan, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 12, pp. 1559–1564.

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Moskalik, M.Y., Astakhova, V.V. & Shainyan, B.A. Oxidative addition of trifluoromethanesulfonamide to cycloalkadienes. Russ J Org Chem 48, 1530–1535 (2012). https://doi.org/10.1134/S1070428012120068

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  • DOI: https://doi.org/10.1134/S1070428012120068

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