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
JF  - 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
U6  - https://doi.org/10.1134/S1070428011090016
SN  - 1070-4280
VL  - 47
IS  - 9
SP  - 1271
EP  - 1277
PB  - Pleiades Publ.
CY  - New York
ER  - 
TY  - JOUR
A1  - Meshcheryakov, Vladimir I.
A1  - Moskalik, Mikail Yu.
A1  - Kelling, Alexandra
A1  - Schilde, Uwe
A1  - Ushakov, Igor A.
A1  - Shainyan, Bagrat A.
T1  - Oxymethylation of trifluoromethanesulfonamide with paraformaldehyde in ethyl acetate
N2  - Acid-catalyzed reaction of trifluoromethanesulfonamide with paraformaldehyde in ethyl acetate led to the formation of oxymethylated products that did not form in the reaction carried out in sulfuric acid. Following products were obtained: 5-trifluoromethylsulfonyl-1,3-dioxazinane, 3,7-bis-(trifluoromethylsulfonyl)-1,5,3,7-dioxadiazocane, and a complex of trifluoromethanesulfonamide with 2,4,8,10-tetraoxospiro[5,5]undecene, 1:1. The spiroring resulted from the cyclization of pentaerythritol under the action of formaldehyde. The pentaerythritol formed in its turn by oxymethylation of the methyl group of ethyl acetate with paraformaldehyde followed by the reduction of the COOEt group into CH2 OH by the formaldehyde.
Y1  - 2008
UR  - http://springer.metapress.com/content/q58m84577ng74p3g/ ?p=0be1219998b44c288f855f33f6168bf6&pi=19
U6  - https://doi.org/10.1134/S1070428008020206
SN  - 1070-4280
ER  -