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Oxidative addition of trifluoromethanesulfonamide to cycloalkadienes

  • In the oxidative system (t-BuOCl+NaI) trifluoromethanesulfonamide is regio- and stereoselectively added to only one double bond of cyclopentadiene and 1,3-cyclohexadiene giving rise to 1,1,1-trifluoro-N-(5-iodocyclopent-2-en-1-yl)methanesulfonamide 7 and trans-N,N'-cyclohex-3-en-1,2-diylbis(1,1,1-trifluoromethanesulfonamide) 8. The structure of 7 and 8 was determined by X-ray, NMR, and MS. With 1,4-cyclohexadiene, addition to both double bonds occurs with the formation of N,N'-(4-chloro-5-iodocyclohexan-1,2-diyl)bis(1,1,1-trifluoromethanesulfonamide) 9. Under the action of sodium iodide in acetone, the latter product undergoes halogenophilic attack with the reduction of the CHI group and elimination of HCl to give trans-N,N'-cyclohex-4-en-1,2-diylbis(1,1,1-trifluoromethanesulfonamide) 10, whose structure was also determined by X-ray analysis. 1,3,5-Cycloheptatriene under these conditions is oxidized to benzaldehyde and does not react with trifluoromethanesulfonamide.

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Author:Mikhail Yu Moskalik, Bagrat A. Shainyan, Vera V. Astakhova, Uwe SchildeORCiDGND
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Place of publication:Oxford
Document Type:Article
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Tag:1,2-Disulfonamides; Allylamides; Cyclodienes; Trifluoromethanesulfonamide; X-ray
First Page:705
Last Page:711
Funder:Russian Foundation for Basic Research; Deutsche Forschungsgemeinschaft [RFBR 10-03-00110, 12-03-31295, RFBR-DFG 11-03-91334]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert