TY  - JOUR
A1  - Moskalik, Mikail Yu.
A1  - Shainyan, Bagrat A.
A1  - Schilde, Uwe
T1  - Reaction of trifluoromethanesulfonamide with alkenes and cycloocta-1,5-diene under oxidative conditions direct assembly of 9-heterobicyclo[4.2.1]nonanes
T2  - Russian journal of organic chemistry
N2  - Reactions of trifluoromethanesulfonamide with alpha-methylstyrene, 2-methylpent-1-ene, and cycloocta-1,5-diene in the system t-BuOCl-NaI were studied. In the reaction with alpha-methylstyrene 1-iodo-2-phenylpropan-2-ol was the only isolated product. The reaction with 2-methylpent-1-ene gave a mixture of N,N'-(2-methylpentane-1,2-diyl)bis(trifluoromethanesulfonamide), trifluoro-N-(2-hydroxy-2-methylpentyl)-methanesulfonamide, and N,N'-[oxybis(2-methylpentan-2,1-diyl)]bis(trifluoromethanesulfonamide). Trifluoromethanesulfonamide reacted with cycloocta-1,5-diene to produce a mixture of 2,5-diiodo-9-(trifluoromethylsulfonyl)-9-azabicyclo[4.2.1]nonane and 2,5-diiodo-9-oxabicyclo[4.2.1]nonane; this reaction may be regarded as the first example of direct assembly of bicyclononane skeleton.
Y1  - 2011
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/36610
SN  - 1070-4280
VL  - 47
IS  - 9
SP  - 1271
EP  - 1277
PB  - Pleiades Publ.
CY  - New York
ER  -