Reactions of Perfluorinated Alkenyl-, Alkynyl-, Alkyltrifluoroborates, and Selected Hydrocarbon Analogues with the Halogenating Agents Hal(2) (Hal = F, Cl, Br), "BrF" (BrF3-Br-2 1:1), and ICl

Reactions of Perfluorinated Alkenyl-, Alkynyl-, Alkyltrifluoroborates, and Selected Hydrocarbon Analogues with the Halogenating Agents Hal(2) (Hal = F, Cl, Br), "BrF" (BrF3-Br-2 1:1), and ICl Full article

Journal

Zeitschrift fur Anorganische und Allgemeine Chemie
ISSN: 0044-2313

Output data

Year: 2012, Volume: 638, Number: 3-4, Pages: 565-579 Pages count : DOI: 10.1002/zaac.201100276

Tags

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

Authors

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

Affiliations

1	(Данные Web of science) Univ Duisburg Essen, Dept Inorgan Chem, D-47048 Duisburg, Germany
2	(Данные Web of science) SB RAS, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
3	(Данные Web of science) SB RAS, GK Boreskov Inst Catalysis, Novosibirsk 630090, Russia

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 [CF2ICFClBF3](-). 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 Hal(2) (Hal = F, Cl, Br), "BrF" (BrF3-Br-2 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

Published online:	Sep 29, 2011
Published print:	Mar 1, 2012

Web of science	WOS:000301783500012
Scopus	2-s2.0-84858761455
Elibrary	17980865
OpenAlex	W2039650372