(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]

(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] Научная публикация

Журнал

Journal of Fluorine Chemistry
ISSN: 0022-1139

Вых. Данные

Год: 2003, Том: 123, Номер: 1, Страницы: 43-49 Страниц : 7 DOI: 10.1016/S0022-1139(03)00107-6

Ключевые слова

methoxyborates; fluoroborates; fluoroalkenes; nucleophilic substitution; stereoselectivity; NMR spectroscopy

Авторы

Frohn HJ ¹ , Bardin VV ²

Организации

1	(Данные Web of science) Gerhard Mercator Univ, Inst Chem, D-47048 Duisburg, Germany
2	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk, SB, Inst Organ Chem, Novosibirsk 630090, Russia

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.

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

Опубликована в печати:

1 сент. 2003 г.

Web of science	WOS:000185522800006
Scopus	2-s2.0-0041784668
РИНЦ	13425634
OpenAlex	W1998245898