ChemInform Abstract: Fluorinated Carbanions. Part 3. (9H-Fluoren-9-ylidene)fluoromethyllithium, a Stabilized Fluoroalkenyl Carbanion. Preparation, Reactions, 13C and 19F NMR Spectra.

ChemInform ◽  
2010 ◽  
Vol 33 (19) ◽  
pp. no-no
Author(s):  
Jaroslav Kvicala ◽  
Andrew Pelter
Tetrahedron ◽  
1990 ◽  
Vol 46 (2) ◽  
pp. 335-340 ◽  
Author(s):  
Charles N. Robinson ◽  
Gregory E. Stablein ◽  
Carl D. Slater

2001 ◽  
Vol 66 (10) ◽  
pp. 1508-1520 ◽  
Author(s):  
Jaroslav Kvíčala ◽  
Andrew Pelter

(9H-Fluoren-9-ylidene)fluoromethyllithium (1) was prepared by a low-temperature transmetallation of bromo(9H-fluoren-9-ylidene)fluoromethane (2). Whereas the synthesis of unlabeled bromofluoroalkene 2a was based on Wittig-Horner reaction of fluorenone (3) with ethyl (diethoxyphosphoryl)fluoroacetate (4), (1-13C)-labeled compound 2b was obtained via an addition of labeled lithium 1-ethoxy-2-fluoro(2-13C)ethen-1-olate (5) to ketone 3. Fluoroethenyllithium 1 was found by a low-temperature 19F NMR spectroscopy to be stable up to -40 °C; it was reacted with the series of electrophiles, e.g. benzaldehyde (6), methyl iodide (7) or chloro(trimethyl)silane (8). 13C NMR experiments with (1-13C)-labeled 1a proved that fluorocarbenoid 1 is probably monomeric in THF solution in analogy to other halocarbenoids.


1972 ◽  
Vol 6 (2) ◽  
pp. 200-208 ◽  
Author(s):  
A De Marco ◽  
G Gatti
Keyword(s):  
19F Nmr ◽  

1985 ◽  
Vol 29 (1-2) ◽  
pp. 191
Author(s):  
Gerhard Hägele ◽  
Winfried Boenigk ◽  
Michael Engelhardt

Chemosphere ◽  
2007 ◽  
Vol 69 (8) ◽  
pp. 1213-1220 ◽  
Author(s):  
P. Liu ◽  
J.D. Goddard ◽  
G. Arsenault ◽  
J. Gu ◽  
A. McAlees ◽  
...  

1998 ◽  
Vol 53 (8) ◽  
pp. 829-832 ◽  
Author(s):  
H. Thomsen ◽  
W. Preetz

Abstract By reaction of closo-[B6H5F]2- in alkaline solution with excess iodine the monofluoropentaiodo- closo-hexaborate anion [B6FI5]2- is formed in good yield. The crystal structure of (CH2Py2)[B6FI5] has been determined by single crystal X-ray diffraction analysis (orthorhombic, space group Pnma, a = 13.803(2), b = 11.759(2), c = 13.936(2) Å, Z = 4). The B-F-bond length is 1.41 Å, the B-I distances range from 2.13 to 2.17 Å, the B-B distances from 1.69 to 1.76 A. According to the C4v point symmetry the 11B NMR spectrum of the anion exhibits three singlets at +3.8,-30.1 and-33.3 ppm with the intensity ratio 1:4:1, the 19F NMR spectrum one quartet at -247.6 ppm with the coupling constant 1J (19F, 11B) = 54 Hz.


1992 ◽  
Vol 191 (2) ◽  
pp. 189-196 ◽  
Author(s):  
B. Armstrong ◽  
A. Grier ◽  
J.B. Hamilton ◽  
H. Khuu ◽  
C.A.L. Mahaffy ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document