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Reaction of trifluoromethanesulfonamide with alkenes and cycloocta-1,5-diene under oxidative conditions direct assembly of 9-heterobicyclo[4.2.1]nonanes

  • 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.

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Author:Mikail Yu. Moskalik, Bagrat A. Shainyan, Uwe SchildeORCiDGND
ISSN:1070-4280 (print)
Parent Title (English):Russian journal of organic chemistry
Publisher:Pleiades Publ.
Place of publication:New York
Document Type:Article
Year of first Publication:2011
Year of Completion:2011
Release Date:2017/03/26
First Page:1271
Last Page:1277
Funder:Russian Foundation for Basic Research; German Research Society [10-03-00 110, 08-03-91 954]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert