Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids

Boettcher T, Steinhauer S, Allefeld N, Hoge B, Neumann B, Stammler H-G, Bassil BS, Winter M, Mitzel NW, Roeschenthaler G-V (2014)
Dalton Transactions 43(7): 2979-2987.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Autor
; ; ; ; ; ; ; ; ;
Abstract / Bemerkung
The crystal structures of the previously reported 2,2-difluoro-1,3-dimethylimidazolidine and its acyclic analog were determined by in situ crystallization. Both liquid fluorinating agents have recently been introduced as potent precursors for the synthesis of p-block element carbene complexes. These fluorine compounds were compared with chloro-amidinium chlorides, which are already established carbene precursors. The chlorides were characterized as ion pairs and contrasted to the previous interpretation as charge-transfer complexes between carbene and dichlorine. Furthermore, the two precursors are used for the synthesis of a series of new carbene complexes of phosphorus( V) fluorides substituted with perfluoroalkyl-groups. These unusually stable hexacoordinate phosphorus( V) complexes were treated with anhydrous hydrogen fluoride to yield imidazolium phosphates. This procedure allows the synthesis of salts used as ionic liquids in high yield and high purity.
Erscheinungsjahr
Zeitschriftentitel
Dalton Transactions
Band
43
Ausgabe
7
Seite(n)
2979-2987
ISSN
eISSN
PUB-ID

Zitieren

Boettcher T, Steinhauer S, Allefeld N, et al. Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions. 2014;43(7):2979-2987.
Boettcher, T., Steinhauer, S., Allefeld, N., Hoge, B., Neumann, B., Stammler, H. - G., Bassil, B. S., et al. (2014). Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions, 43(7), 2979-2987. doi:10.1039/c3dt53043d
Boettcher, T., Steinhauer, S., Allefeld, N., Hoge, B., Neumann, B., Stammler, H. - G., Bassil, B. S., Winter, M., Mitzel, N. W., and Roeschenthaler, G. - V. (2014). Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions 43, 2979-2987.
Boettcher, T., et al., 2014. Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions, 43(7), p 2979-2987.
T. Boettcher, et al., “Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids”, Dalton Transactions, vol. 43, 2014, pp. 2979-2987.
Boettcher, T., Steinhauer, S., Allefeld, N., Hoge, B., Neumann, B., Stammler, H.-G., Bassil, B.S., Winter, M., Mitzel, N.W., Roeschenthaler, G.-V.: Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions. 43, 2979-2987 (2014).
Boettcher, Tobias, Steinhauer, Simon, Allefeld, Nadine, Hoge, Berthold, Neumann, Beate, Stammler, Hans-Georg, Bassil, Bassem S., Winter, Martin, Mitzel, Norbert W., and Roeschenthaler, Gerd-Volker. “Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids”. Dalton Transactions 43.7 (2014): 2979-2987.

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Closing the Gap: Structural Evidence for the Missing Hexabromide Dianion [Br6 ]2.
Sonnenberg K, Pröhm P, Müller C, Beckers H, Steinhauer S, Lentz D, Riedel S., Chemistry 24(5), 2018
PMID: 29244220

55 References

Daten bereitgestellt von Europe PubMed Central.


Arduengo, J. Am. Chem. Soc. 113(), 1991

Arduengo, Acc. Chem. Res. 32(), 1999

Herrmann, Angew. Chem., Int. Ed. Engl. 36(), 1997

Hahn, Angew. Chem., Int. Ed. 47(), 2008

Crudden, Coord. Chem. Rev. 248(), 2004

Droge, Angew. Chem., Int. Ed. 49(), 2010

Herrmann, Angew. Chem., Int. Ed. Engl. 34(), 1995

Herrmann, Angew. Chem., Int. Ed. 41(), 2002

Cazin, 2011

Nolan, 2006
N-heterocyclic carbenes in late transition metal catalysis.
Diez-Gonzalez S, Marion N, Nolan SP., Chem. Rev. 109(8), 2009
PMID: 19588961

Marion, Angew. Chem. 119(), 2007

Marion, Angew. Chem., Int. Ed. 46(), 2007

de, Coord. Chem. Rev. 253(), 2009

Glorius, 2007

Arduengo, Tetrahedron 55(), 1999

Peris, 2007

Kuhn, Coord. Chem. Rev. 249(), 2005

Kirmse, Eur. J. Org. Chem. (), 2005
Chemistry. Soluble allotropes of main-group elements.
Dyker CA, Bertrand G., Science 321(5892), 2008
PMID: 18719272
A stable silicon(0) compound with a Si=Si double bond.
Wang Y, Xie Y, Wei P, King RB, Schaefer HF 3rd, von R Schleyer P, Robinson GH., Science 321(5892), 2008
PMID: 18719279

Sidiropoulos, Angew. Chem., Int. Ed. 48(), 2009
An N-heterocyclic carbene adduct of diatomic tin, :Sn=Sn:.
Jones C, Sidiropoulos A, Holzmann N, Frenking G, Stasch A., Chem. Commun. (Camb.) 48(79), 2012
PMID: 22933046
Carbene-stabilized diphosphorus.
Wang Y, Xie Y, Wei P, King RB, Schaefer HF 3rd, Schleyer Pv, Robinson GH., J. Am. Chem. Soc. 130(45), 2008
PMID: 18937460

Abraham, Chem.–Eur. J. 16(), 2010
Ambient-temperature isolation of a compound with a boron-boron triple bond.
Braunschweig H, Dewhurst RD, Hammond K, Mies J, Radacki K, Vargas A., Science 336(6087), 2012
PMID: 22700924
Carbene stabilization of highly reactive main-group molecules.
Wang Y, Robinson GH., Inorg Chem 50(24), 2011
PMID: 21634365
Carbene-stabilized main group diatomic allotropes.
Wang Y, Robinson GH., Dalton Trans 41(2), 2011
PMID: 21904737

Böttcher, Organometallics 31(), 2012

Böttcher, Chem. Sci. 4(), 2013

Denk, Angew. Chem., Int. Ed. Engl. 36(), 1997

Alder, Angew. Chem., Int. Ed. Engl. 35(), 1996

Dippel, J. Electrochem. Soc. 159(), 2012

Pajkert, Tetrahedron 69(), 2013

Hayashi, Chem. Commun. (), 2002

Fürstner, Organometallics 22(), 2003

Kremzow, Chem.–Eur. J. 11(), 2005

Fink, J. Chem. Phys. 71(), 1979

Ghosh, J. Chem. Phys. 20(), 1952

Cole, New J. Chem. 26(), 2002

Kuhn, Z. Anorg. Allg. Chem. 628(), 2002

Tiritiris, Z. Kristallogr. 223(), 2008

Fujisawa, Chem. Lett. (), 1982

Petrov, Zh. Strukt. Khim. (), 1985

Petrov, J. Struct. Chem. 26(), 1985

Herzberg, 1950

Shibata, J. Phys. Chem. 67(), 1963

Donohue, Acta Crystallogr., Sect. A: Found. Crystallogr. 18(), 1965

Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 64(), 2008

Kolomeitsev, J. Fluorine Chem. 103(), 2000

Isobe, J. Org. Chem. 64(), 1999

Zakharov, 0

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 24346352
PubMed | Europe PMC

Suchen in

Google Scholar