(Fluoroorgano)fluoroboranes and -borates - Part 10 - The unusual reactivity of C3F7OCF=CF2 with PBu3 and the complex hydrides M[EH4] (M : Li, Na; E : B, Al); preparation of potassium perfluoro-2-propoxyeth-1-enyltrifluoroborate K[C3F7OCF=CFBF3] Full article
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Journal of Fluorine Chemistry
ISSN: 0022-1139 |
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| Output data | Year: 2003, Volume: 123, Number: 1, Pages: 43-49 Pages count : 7 DOI: 10.1016/S0022-1139(03)00107-6 | ||||
| Tags | methoxyborates; fluoroborates; fluoroalkenes; nucleophilic substitution; stereoselectivity; NMR spectroscopy | ||||
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Abstract:
The nucleophilic hydrode fluorination of C3F7OCF=CF2 with the complex hydrides Li[AlH4], Li[BH4] or Na[BH4] proceeded nonstereoselectively and was accompanied by the formation of either cis- and trans-C3F7OCH=CFH and/or C3F7OCHFCF2H. The reaction of C3F7OCF=CF2 with PBu3 followed by treatment with BF3.OMe2 or BF3.OEt2 yielded [C3F7OCF=CFPBu3] [BF4] (cis and trans) and, probably, [trans-Bu3PCF=CFPBu3] [BF4](2). The hydrolysis of the latter with pure water proceeded quickly while the former isomeric mixture formed the isomeric olefins C3F7OCF=CFH slowly. The usage of aqueous NaOH instead of water produced mainly trans-CHF=CHF. The metallation of C3F7OCF=CFH (cis:trans = 45:55) to C3F7OCF=CFLi and its subsequent reaction with B(OMe)(3) and K[HF2] gave the salt K[C3F7OCF=CFBF3] in a different cis to trans ratio (25:75) with satisfactory yield. (C) 2003 Elsevier Science B.V. All rights reserved.
Cite:
Frohn H.
, Bardin V.
(Fluoroorgano)fluoroboranes and -borates - Part 10 - The unusual reactivity of C3F7OCF=CF2 with PBu3 and the complex hydrides M[EH4] (M : Li, Na; E : B, Al); preparation of potassium perfluoro-2-propoxyeth-1-enyltrifluoroborate K[C3F7OCF=CFBF3]
Journal of Fluorine Chemistry. 2003. V.123. N1. P.43-49. DOI: 10.1016/S0022-1139(03)00107-6 WOS Scopus РИНЦ OpenAlex
(Fluoroorgano)fluoroboranes and -borates - Part 10 - The unusual reactivity of C3F7OCF=CF2 with PBu3 and the complex hydrides M[EH4] (M : Li, Na; E : B, Al); preparation of potassium perfluoro-2-propoxyeth-1-enyltrifluoroborate K[C3F7OCF=CFBF3]
Journal of Fluorine Chemistry. 2003. V.123. N1. P.43-49. DOI: 10.1016/S0022-1139(03)00107-6 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Sep 1, 2003 |
Identifiers:
| Web of science: | WOS:000185522800006 |
| Scopus: | 2-s2.0-0041784668 |
| Elibrary: | 13425634 |
| OpenAlex: | W1998245898 |