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 Full article
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Zeitschrift fur Anorganische und Allgemeine Chemie
ISSN: 0044-2313 , E-ISSN: 1521-3749 |
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| Output data | Year: 2012, Volume: 638, Number: 3-4, Pages: 565-579 Pages count : 15 DOI: 10.1002/zaac.201100276 | ||||||
| Tags | 1, 2-Halogen addition, Alkenyltrifluoroborates, Alkyltrifluoroborates, Alkynyltrifluoroborates, Bromofluorination, Halodeboration, NMR spectroscopy, Stereospecifity | ||||||
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| Affiliations |
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Funding (3)
| 1 | Russian Foundation for Basic Research | |
| 2 | German Research Foundation | |
| 3 | Verband der Chemischen Industrie |
Abstract:
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.
Cite:
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 ANCAN OpenAlex
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 ANCAN OpenAlex
Dates:
| Submitted: | Jun 21, 2011 |
| Accepted: | Sep 29, 2011 |
| Published online: | Sep 29, 2011 |
| Published print: | Mar 1, 2012 |
Identifiers:
| Web of science: | WOS:000301783500012 |
| Scopus: | 2-s2.0-84858761455 |
| Elibrary: | 17980865 |
| Chemical Abstracts: | 2012:444659 |
| Chemical Abstracts (print): | 157:12862 |
| OpenAlex: | W2039650372 |