Bromination of highly unsaturated trifluoromethanesulfonamide derivatives

Verfasser / Beitragende:
[B. Shainyan, I. Ushakova, Yu. Danilevich]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/7(2015-07-01), 931-935
Format:
Artikel (online)
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024 7 0 |a 10.1134/S1070428015070064  |2 doi 
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245 0 0 |a Bromination of highly unsaturated trifluoromethanesulfonamide derivatives  |h [Elektronische Daten]  |c [B. Shainyan, I. Ushakova, Yu. Danilevich] 
520 3 |a 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. 
540 |a Pleiades Publishing, Ltd., 2015 
700 1 |a Shainyan  |D B.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
700 1 |a Ushakova  |D I.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
700 1 |a Danilevich  |D Yu  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/7(2015-07-01), 931-935  |x 1070-4280  |q 51:7<931  |1 2015  |2 51  |o 11178 
856 4 0 |u https://doi.org/10.1134/S1070428015070064  |q text/html  |z Onlinezugriff via DOI 
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950 |B NATIONALLICENCE  |P 700  |E 1-  |a Shainyan  |D B.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Ushakova  |D I.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Danilevich  |D Yu  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/7(2015-07-01), 931-935  |x 1070-4280  |q 51:7<931  |1 2015  |2 51  |o 11178