@article{MoskalikShainyanAstakhovaetal.2013, author = {Moskalik, Mikhail Yu and Shainyan, Bagrat A. and Astakhova, Vera V. and Schilde, Uwe}, title = {Oxidative addition of trifluoromethanesulfonamide to cycloalkadienes}, series = {Tetrahedron}, volume = {69}, journal = {Tetrahedron}, number = {2}, publisher = {Elsevier}, address = {Oxford}, issn = {0040-4020}, doi = {10.1016/j.tet.2012.10.099}, pages = {705 -- 711}, year = {2013}, abstract = {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.}, language = {en} } @article{ShainyanMoskalikAstakhovaetal.2014, author = {Shainyan, Bagrat A. and Moskalik, Mikhail Yu and Astakhova, Vera V. and Schilde, Uwe}, title = {Novel design of 3,8-diazabicyclo[3.2.1]octane framework in oxidative sulfonamidation of 1,5-hexadiene}, series = {Tetrahedron}, volume = {70}, journal = {Tetrahedron}, number = {30}, publisher = {Elsevier}, address = {Oxford}, issn = {0040-4020}, doi = {10.1016/j.tet.2014.04.095}, pages = {4547 -- 4551}, year = {2014}, abstract = {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.}, language = {en} } @article{ShainyanMoskalikHeydenreichetal.2014, author = {Shainyan, Bagrat A. and Moskalik, Mikhail Yu and Heydenreich, Matthias and Kleinpeter, Erich}, title = {Conformational equilibrium and dynamic behavior of bis-N-triflyl substituted 3,8-diazabicyclo[3.2.1]octane}, series = {Magnetic resonance in chemistry}, volume = {52}, journal = {Magnetic resonance in chemistry}, number = {8}, publisher = {Wiley-Blackwell}, address = {Hoboken}, issn = {0749-1581}, doi = {10.1002/mrc.4086}, pages = {448 -- 452}, year = {2014}, abstract = {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.}, language = {en} }