Synthesis and bromination/dehydrobromination of <Emphasis Type="Italic">N,N</Emphasis>-diallyltrifluoromethanesulfonamide |
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Authors: | B A Shainyan Yu S Danilevich I A Ushakov |
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Institution: | 1.Favorskii Irkutsk Institute of Chemistry, Siberian Branch,Russian Academy of Sciences,Irkutsk,Russia |
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Abstract: | The reaction of triflluoromethanesulfonamide with allyl bromide in dimethyl sulfoxide gave N,N-diallyltrifluoromethanesulfonamide which was subjected to bromination with 1 and 2 equiv of bromine. The product of bromine addition to both allyl groups, CF3SO2N(CH2CHBrCH2Br)2, was found to exist as a mixture of two diastereoisomers at a ratio of 9: 11. Its dehydrobromination by the action of sodium methoxide was chemoselective with successive elimination of one, two, and three hydrogen bromide molecules to afford N-(2-bromoprop-2-en-1-yl)-N-(2,3-dibromopropyl)trifluoromethanesulfonamide, N,N-bis(2-bromoprop-2-en-1-yl)trifluoromethanesulfonamide, and N-(2-bromoprop-2-en-1-yl)-N-(propadienyl)trifluoromethanesulfonamide, respectively. |
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