TY  - JOUR
A1  - Moskalik, Mikhail Yu
A1  - Shainyan, Bagrat A.
A1  - Astakhova, Vera V.
A1  - Schilde, Uwe
T1  - Oxidative addition of trifluoromethanesulfonamide to cycloalkadienes
JF  - Tetrahedron
N2  - 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.
KW  - Trifluoromethanesulfonamide
KW  - Cyclodienes
KW  - 1,2-Disulfonamides
KW  - Allylamides
KW  - X-ray
Y1  - 2013
U6  - https://doi.org/10.1016/j.tet.2012.10.099
SN  - 0040-4020
VL  - 69
IS  - 2
SP  - 705
EP  - 711
PB  - Elsevier
CY  - Oxford
ER  -