The hydrofluorocarbon 1,1,1,2-tetrafluoroethane (HFC-134a) as a ready source of trifluorovinyllithium

Abstract

Trifluorovinyllithium has been synthesised in high yield from 1,1,1,2-tetrafluoroethane (HFC 134a) by treatment with butyllithium at -78 "C, and then treated with a variety of electrophiles in one-pot reactions.

Insight into the Reactions of Trifluorovinylsilanes with Aromatic Aldehydes

“…The following products were synthesized according to literature procedures: Me 3-SiCF=CF 2 , [12] Et 3 SiCF=CF 2 , [12] [Me 4 N]F, [13] 2-fluoro-3-p-tolylallylic acid fluoride (7a). [7] All solvents were purified according to literature procedures.…”

C6F5XeF, a versatile starting material in xenon–carbon chemistry

“…CF 3 SiMe 3 was purchased from Aldrich, and CF 2 ¼ CFSiMe 3 was synthesised by the reaction of CF 3 CH 2 F in Et 2 O with two equivalent of BuLi/n-hexane at À60 8C and subsequent reaction with Me 3 SiCl at À78 8C. [17] 19 F À89.0, dd, 3 J(F-2trans, F-2cis) 70, 3 J(F-2trans, F-1) 25 Hz, F-2trans; À118.3, dd, 3 J(F-2cis, F-1) 117 Hz, F-2cis; À200.0, dd, F-1.…”

The synthesis and structural characterisation of an homologous series of group 14 1-chloro-2,2-difluorovinyl compounds

“…Over the past decade, this has led to the development of novel synthetic protocols for introducing fluorovinyl-based units, derived from commercially available hydrofluorocarbon (HFC) or hydrochlorofluorocarbon (HCFC) precursors, via the respective lithium reagents. The trifluorovinyl unit (-CF¼CF 2 ) can thus be readily introduced into a wide range of substrates using trifluorovinyllithium (LiCF¼CF 2 ), which is generated from the reaction of 1,1,1,2-tetrafluoroethane (HFC-134a) with 2 equivalents of n-butyllithium, [4] whilst the analogous 1-chloro-2, 2-difluorovinyl systems (-CCl¼CF 2 ) can be similarly derived from 1-chloro-2,2,2-trifluoroethane (HCFC-133a) [5].…”