Reactions of Perfluorinated Alkenyl-, Alkynyl-, Alkyltrifluoroborates, and Selected Hydrocarbon Analogues with the Halogenating Agents Hal2 (Hal = F, Cl, Br), “BrF” (BrF3–Br2 1:1), and ICl | Sciact - CRIS-система Института катализа

Reactions of Perfluorinated Alkenyl-, Alkynyl-, Alkyltrifluoroborates, and Selected Hydrocarbon Analogues with the Halogenating Agents Hal2 (Hal = F, Cl, Br), “BrF” (BrF3–Br2 1:1), and ICl Научная публикация

Журнал

Zeitschrift fur Anorganische und Allgemeine Chemie
ISSN: 0044-2313 , E-ISSN: 1521-3749

Вых. Данные

Год: 2012, Том: 638, Номер: 3-4, Страницы: 565-579 Страниц : 15 DOI: 10.1002/zaac.201100276

Ключевые слова

1, 2-Halogen addition, Alkenyltrifluoroborates, Alkyltrifluoroborates, Alkynyltrifluoroborates, Bromofluorination, Halodeboration, NMR spectroscopy, Stereospecifity

Авторы

Bardin Vadim V. ¹ , Adonin Nicolay Yu. ^1,2 , Frohn Hermann-Josef ³

Организации

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, SB RAS, Acad. Lavrentjev Avenue 9, 630090 Novosibirsk, Russia
2	G. K. Boreskov Institute of Catalysis, SB RAS Acad. Lavrentjev Avenue 5, 630090 Novosibirsk, Russia
3	Inorganic Chemistry Department, University of Duisburg-Essen, Lotharstrasse 1, 47048 Duisburg, Germany

Информация о финансировании (3)

1	Российский фонд фундаментальных исследований
2	German Research Foundation
3	Verband der Chemischen Industrie

Reactions of [Bu4N][RBF3] [R = CnF2n+1CF=CF (cis, trans), CF2=CF, CF2=C(CF3), trans-C4H9CF=CF, trans-C6H5CF=CF, C4H9CH=CH (cis, trans), CF3C≡C, and C4H9C≡C] with chlorine, bromine, BrF3 + Br2 (as equivalent of “BrF”), and ICl in solution (CH2Cl2, CHCl3, CF3CH2CF2CH3) led to 1, 2-addition of halogen and/or replacement of boron by halogen (halodeboration). The reaction of [Bu4N][CF3C≡CBF3] with less than equimolar amounts of diluted fluorine (5 %) in 1, 1, 1, 3, 3-pentafluorobutane (PFB) showed only [Bu4N][CF3CF2CF2BF3] as fluorine addition product besides extensive fluorodeboration. Suspensions of the insoluble K[CF2=CFBF3] salt reacted with Cl2 and Br2 in CH2Cl2 giving preferentially products of halogen addition across the C=C bond. In reactions with ICl iododeboration with formation of CF2=CFI occurred besides 1, 2-addition with formation of [CF2I–CFClBF3]–. The halodeboration reaction of[Bu4N][trans-C4H9CF=CFBF3] with Br2, “BrF”, and ICl, of K[trans-C6H5CF=CFBF3] with Br2, and of [Bu4N][trans-C4F9CF=CFBF3] with ICl proceeded stereospecifically.

Bardin V.V. , Adonin N.Y. , Frohn H-J.
Reactions of Perfluorinated Alkenyl-, Alkynyl-, Alkyltrifluoroborates, and Selected Hydrocarbon Analogues with the Halogenating Agents Hal2 (Hal = F, Cl, Br), “BrF” (BrF3–Br2 1:1), and ICl
Zeitschrift fur Anorganische und Allgemeine Chemie. 2012. V.638. N3-4. P.565-579. DOI: 10.1002/zaac.201100276 WOS Scopus РИНЦ CAPlusCA OpenAlex

Поступила в редакцию:	21 июн. 2011 г.
Принята к публикации:	29 сент. 2011 г.
Опубликована online:	29 сент. 2011 г.
Опубликована в печати:	1 мар. 2012 г.

Web of science:	WOS:000301783500012
Scopus:	2-s2.0-84858761455
РИНЦ:	17980865
Chemical Abstracts:	2012:444659
Chemical Abstracts (print):	157:12862
OpenAlex:	W2039650372

БД	Цитирований
Web of science	6
Scopus	7
РИНЦ	7
OpenAlex	9