caa a22 4500 605529469 CHVBK 20210128100818.0 cr unu---uuuuu 210128e20150701xx s 000 0 eng 10.1134/S1070428015070064 doi (NATIONALLICENCE)springer-10.1134/S1070428015070064 Bromination of highly unsaturated trifluoromethanesulfonamide derivatives [Elektronische Daten] [B. Shainyan, I. Ushakova, Yu. Danilevich] 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′-[(2E,4E)-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. Pleiades Publishing, Ltd., 2015 Shainyan B. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Ushakova I. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Danilevich Yu Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Russian Journal of Organic Chemistry Pleiades Publishing 51/7(2015-07-01), 931-935 1070-4280 51:7<931 2015 51 11178 https://doi.org/10.1134/S1070428015070064 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015070064 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Shainyan B. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 700 1- Ushakova I. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 700 1- Danilevich Yu Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/7(2015-07-01), 931-935 1070-4280 51:7<931 2015 51 11178