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  - 
TY  - JOUR
A1  - Shainyan, Bagrat A.
A1  - Moskalik, Mikhail Yu
A1  - Astakhova, Vera V.
A1  - Schilde, Uwe
T1  - Novel design of 3,8-diazabicyclo[3.2.1]octane framework in oxidative sulfonamidation of 1,5-hexadiene
JF  - Tetrahedron
N2  - 1,5-Hexadiene reacts with trifluoromethanesulfonamide in the oxidative system (t-BuOCl+Nal) to give trans-2,5-bis(iodomethyl)-1-(trifluoromethylsulfonyl)pyrrolidine 5 and 3,8-bis(trifluoromethylsulfonyl)-3,8-diazabicyclo[3.2.1]octane 6. With arenesulfonamides ArSO2NH2 (Ar=Ph, Tol), the reaction stops at the formation of the trans and cis isomers of 2,5-bis(iodomethyl)-1-(arenesulfonyl)pyrrolidine 7 and 8 (1:1). The cis isomers of 7 and 8 do not undergo cyclization to the corresponding 3,8-disubstituted 3,8-diazabicyclo[3.2.1]octanes. The reaction with triflamide represents the first example of one-pot two-step route to 3,8-diazabicyclo[3.2.1]octane system. (C) 2014 Elsevier Ltd. All rights reserved.
KW  - Trifluoromethanesulfonamide
KW  - Arenesulfonamides
KW  - 1,5-Dienes
KW  - Cycloaddition
KW  - 3,8-Diazabicyclo[3.2.1]octane
KW  - X-ray
Y1  - 2014
U6  - https://doi.org/10.1016/j.tet.2014.04.095
SN  - 0040-4020
VL  - 70
IS  - 30
SP  - 4547
EP  - 4551
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Shainyan, Bagrat A.
A1  - Moskalik, Mikhail Yu
A1  - Heydenreich, Matthias
A1  - Kleinpeter, Erich
T1  - Conformational equilibrium and dynamic behavior of bis-N-triflyl substituted 3,8-diazabicyclo[3.2.1]octane
JF  - Magnetic resonance in chemistry
N2  - Restricted rotation about the N-S partial double bonds in a bis-N-triflyl substituted 3,8-diazabicyclo[3.2.1]octane derivative 1 has been frozen at low temperature (Delta G* = 11.6 kcal mol(-1)), and the existence of all four rotamers about the two N-S bonds, 3-in, 8-in, 3-in, 8-out, 3-out, 8-in, and 3-out, 8-out, respectively, proved experimentally by NMR spectroscopy and theoretically by DFT and MP2 calculations. Copyright (C) 2014 John Wiley & Sons, Ltd.
KW  - NMR
KW  - H-1
KW  - C-13
KW  - F-19
KW  - Dynamic NMR
KW  - Conformational equilibrium
KW  - restricted N-S rotation
Y1  - 2014
U6  - https://doi.org/10.1002/mrc.4086
SN  - 0749-1581
SN  - 1097-458X
VL  - 52
IS  - 8
SP  - 448
EP  - 452
PB  - Wiley-Blackwell
CY  - Hoboken
ER  -