학술논문
Bromination of highly unsaturated trifluoromethanesulfonamide derivatives.
Document Type
Article
Author
Source
Subject
*BROMINATION
*UNSATURATED compounds
*SULFONAMIDES
*CHEMICAL derivatives
*RING formation (Chemistry)
*CARBON-carbon bonds
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Language
ISSN
1070-4280
Abstract
The bromination of trifluoro- N-(prop-2-yn-1-yl)methanesulfonamide with molecular bromine gives a mixture of Z- and E-isomeric N-(2,3-dibromoprop-2-en-1-yl)trifluoromethanesulfonamides, regardless of the reaction conditions. Bromine adds to both triple bonds of trifluoro- N, N-bis(prop-2-yn-1-yl)methanesulfonamide, yielding a mixture of N-(2,3-dibromprop-2-en-1-yl)trifluoro- N-(prop-2-yn-1-yl)methanesulfonamide, N, N-bis(2,3-dibromoprop-2-en-1-yl)trifluoromethanesulfonamide, and trifluoro- N, N-bis(2,2,3,3-tetrabromopropyl) methanesulfonamide. Diacetylenic trifluoromethanesulfonamide derivative, N, N′-hexa-2,4-diyne-1,6-diylbis( trifluoromethanesulfonamide), reacts with bromine to afford N, N′-[(2 E,4 E)-2,3,4,5-tetrabromohexa-2,4-diene-1,6-diyl]bis(trifluoromethanesulfonamide) and isomeric N-(2,3-dibromoprop-2-en-1-yl)trifluoromethanesulfonamides resulting from reductive cleavage of the central C-C bond in the former. [ABSTRACT FROM AUTHOR]