N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid
Rottschäfer D, Neumann B, Stammler H-G, Ghadwal R (2017)
CHEMISTRY-A EUROPEAN JOURNAL 23(38): 9044-9047.
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Abstract / Bemerkung
Four-membered biradicaloid compounds containing a N2E2 (E = main group element) framework have been thoroughly investigated; however, the synthesis of stable analogues with a C2P2 skeleton remains a challenge. Base-mediated double C-H functionalization of IPr = CH2 (1) (IPr = C[N(2,6-iPr(2)-C6H3) CH](2)) with PCl3 affords [{(IPr) CP}(2)Cl]Cl (2) as a royal blue solid. Treatment of 2 with KC8 yields the stable phosphorus biradicaloid [(IPr) CP](2) (3) featuring a four-membered C2P2 ring. Compound 3 is diamagnetic and shows sharp and temperature-independent NMR resonances, revealing its singlet biradicaloid nature. The stability of 3 is attributed to the sigma- and pi-electron-donating property of the N-heterocyclic vinylidene [(IPr) C] group.
Stichworte
carbenes;
heterocycles;
phosphorus;
vinylidenes
Erscheinungsjahr
2017
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
23
Ausgabe
38
Seite(n)
9044-9047
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2912971
Zitieren
Rottschäfer D, Neumann B, Stammler H-G, Ghadwal R. N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL. 2017;23(38):9044-9047.
Rottschäfer, D., Neumann, B., Stammler, H. - G., & Ghadwal, R. (2017). N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL, 23(38), 9044-9047. doi:10.1002/chem.201702433
Rottschäfer, Dennis, Neumann, Beate, Stammler, Hans-Georg, and Ghadwal, Rajendra. 2017. “N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid”. CHEMISTRY-A EUROPEAN JOURNAL 23 (38): 9044-9047.
Rottschäfer, D., Neumann, B., Stammler, H. - G., and Ghadwal, R. (2017). N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL 23, 9044-9047.
Rottschäfer, D., et al., 2017. N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL, 23(38), p 9044-9047.
D. Rottschäfer, et al., “N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 23, 2017, pp. 9044-9047.
Rottschäfer, D., Neumann, B., Stammler, H.-G., Ghadwal, R.: N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL. 23, 9044-9047 (2017).
Rottschäfer, Dennis, Neumann, Beate, Stammler, Hans-Georg, and Ghadwal, Rajendra. “N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid”. CHEMISTRY-A EUROPEAN JOURNAL 23.38 (2017): 9044-9047.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
3 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Biradicaloid and Zwitterion Reactivity of Dicarbondiphosphide Stabilized with N-Heterocyclic Carbenes.
Li Z, Hou Y, Li Y, Hinz A, Chen X., Chemistry 24(19), 2018
PMID: 29247461
Li Z, Hou Y, Li Y, Hinz A, Chen X., Chemistry 24(19), 2018
PMID: 29247461
The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry.
Rottschäfer D, Ebeler F, Strothmann T, Neumann B, Stammler HG, Mix A, Ghadwal RS., Chemistry 24(15), 2018
PMID: 29363830
Rottschäfer D, Ebeler F, Strothmann T, Neumann B, Stammler HG, Mix A, Ghadwal RS., Chemistry 24(15), 2018
PMID: 29363830
N-Heterocyclic Carbene Analogues of Thiele and Chichibabin Hydrocarbons.
Rottschäfer D, Ho NKT, Neumann B, Stammler HG, van Gastel M, Andrada DM, Ghadwal RS., Angew Chem Int Ed Engl 57(20), 2018
PMID: 29668119
Rottschäfer D, Ho NKT, Neumann B, Stammler HG, van Gastel M, Andrada DM, Ghadwal RS., Angew Chem Int Ed Engl 57(20), 2018
PMID: 29668119
78 References
Daten bereitgestellt von Europe PubMed Central.
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 2001
Halliwell, 2015
AUTHOR UNKNOWN, 0
Breher, Coord. Chem. Rev. 251(), 2007
Odd-electron bonds and biradicals in main group element chemistry.
Grutzmacher H, Breher F., Angew. Chem. Int. Ed. Engl. 41(21), 2002
PMID: 12412065
Grutzmacher H, Breher F., Angew. Chem. Int. Ed. Engl. 41(21), 2002
PMID: 12412065
AUTHOR UNKNOWN, Angew. Chem. 114(), 2002
Salem, Angew. Chem. Int. Ed. Engl. 11(), 1972
AUTHOR UNKNOWN, Angew. Chem. 84(), 1972
AUTHOR UNKNOWN, 0
Newcomb, 2005
Berson, 2005
Roth, 2005
AUTHOR UNKNOWN, 0
Cyclic (alkyl)(amino)carbenes (CAACs): stable carbenes on the rise.
Soleilhavoup M, Bertrand G., Acc. Chem. Res. 48(2), 2014
PMID: 25515548
Soleilhavoup M, Bertrand G., Acc. Chem. Res. 48(2), 2014
PMID: 25515548
Isolation and Characterization of a Bismuth(II) Radical.
Schwamm RJ, Harmer JR, Lein M, Fitchett CM, Granville S, Coles MP., Angew. Chem. Int. Ed. Engl. 54(36), 2015
PMID: 26215838
Schwamm RJ, Harmer JR, Lein M, Fitchett CM, Granville S, Coles MP., Angew. Chem. Int. Ed. Engl. 54(36), 2015
PMID: 26215838
AUTHOR UNKNOWN, Angew. Chem. 127(), 2015
Carbene-Stabilized Main Group Radicals and Radical Ions.
Martin CD, Soleilhavoup M, Bertrand G., Chem Sci 4(8), 2013
PMID: 23878717
Martin CD, Soleilhavoup M, Bertrand G., Chem Sci 4(8), 2013
PMID: 23878717
Silicon based radicals, radical ions, diradicals and diradicaloids.
Chandra Mondal K, Roy S, Roesky HW., Chem Soc Rev 45(4), 2015
PMID: 26585359
Chandra Mondal K, Roy S, Roesky HW., Chem Soc Rev 45(4), 2015
PMID: 26585359
Michl, Tetrahedron 44(), 1988
Niecke, Angew. Chem. Int. Ed. Engl. 34(), 1995
AUTHOR UNKNOWN, Angew. Chem. 107(), 1995
AUTHOR UNKNOWN, 0
Valence Isomerization of a 1,3-Diphosphacyclobutane-2,4-diyl: Photochemical Ring Closure to 2,4-diphosphabicyclo
Niecke E, Fuchs A, Nieger M., Angew. Chem. Int. Ed. Engl. 38(20), 1999
PMID: 10540410
Niecke E, Fuchs A, Nieger M., Angew. Chem. Int. Ed. Engl. 38(20), 1999
PMID: 10540410
AUTHOR UNKNOWN, Angew. Chem. 111(), 1999
1,3-Diphosphacyclobutane-2,4-diyl-2-ylidenide: A Unique Carbene and Its Trimethylalane Complex.
Niecke E, Fuchs A, Nieger M, Schmidt O, Schoeller WW., Angew. Chem. Int. Ed. Engl. 38(20), 1999
PMID: 10540411
Niecke E, Fuchs A, Nieger M, Schmidt O, Schoeller WW., Angew. Chem. Int. Ed. Engl. 38(20), 1999
PMID: 10540411
AUTHOR UNKNOWN, Angew. Chem. 111(), 1999
Synthesis of a 1,3-diphosphacyclobutane-2,4-diyl from Mes*C[triple bond]P.
Sugiyama H, Ito S, Yoshifuji M., Angew. Chem. Int. Ed. Engl. 42(32), 2003
PMID: 12923849
Sugiyama H, Ito S, Yoshifuji M., Angew. Chem. Int. Ed. Engl. 42(32), 2003
PMID: 12923849
AUTHOR UNKNOWN, Angew. Chem. 115(), 2003
AUTHOR UNKNOWN, 0
Singlet diradicals: from transition states to crystalline compounds.
Scheschkewitz D, Amii H, Gornitzka H, Schoeller WW, Bourissou D, Bertrand G., Science 295(5561), 2002
PMID: 11884750
Scheschkewitz D, Amii H, Gornitzka H, Schoeller WW, Bourissou D, Bertrand G., Science 295(5561), 2002
PMID: 11884750
Thermal valence isomerization of 2,3-diborata-1,4-diphosphoniabuta-1,3-dienes to bicyclo[1.1.0]butanes and cyclobutane-1,3-diyls.
Bourg JB, Rodriguez A, Scheschkewitz D, Gornitzka H, Bourissou D, Bertrand G., Angew. Chem. Int. Ed. Engl. 46(30), 2007
PMID: 17592605
Bourg JB, Rodriguez A, Scheschkewitz D, Gornitzka H, Bourissou D, Bertrand G., Angew. Chem. Int. Ed. Engl. 46(30), 2007
PMID: 17592605
AUTHOR UNKNOWN, Angew. Chem. 119(), 2007
Snapshots of the Al-Al sigma-bond formation starting from {AlR2} units: experimental and computational observations.
Henke P, Pankewitz T, Klopper W, Breher F, Schnockel H., Angew. Chem. Int. Ed. Engl. 48(43), 2009
PMID: 19708044
Henke P, Pankewitz T, Klopper W, Breher F, Schnockel H., Angew. Chem. Int. Ed. Engl. 48(43), 2009
PMID: 19708044
AUTHOR UNKNOWN, Angew. Chem. 121(), 2009
Synthesis and characterization of the non-Kekule, singlet biradicaloid Ar'Ge(micro-NSiMe(3))(2)GeAr' (Ar' = 2,6-Dipp(2)C(6)H(3), Dipp = 2,6-i-Pr(2)C(6)H(3)).
Cui C, Brynda M, Olmstead MM, Power PP., J. Am. Chem. Soc. 126(21), 2004
PMID: 15161252
Cui C, Brynda M, Olmstead MM, Power PP., J. Am. Chem. Soc. 126(21), 2004
PMID: 15161252
A 1,3-diaza-2,4-distannacyclobutanediide: synthesis, structure, and bonding.
Cox H, Hitchcock PB, Lappert MF, Pierssens LJ., Angew. Chem. Int. Ed. Engl. 43(34), 2004
PMID: 15340953
Cox H, Hitchcock PB, Lappert MF, Pierssens LJ., Angew. Chem. Int. Ed. Engl. 43(34), 2004
PMID: 15340953
AUTHOR UNKNOWN, Angew. Chem. 116(), 2004
Access to a stable Si2N2 four-membered ring with non-Kekule singlet biradical character from a disilyne.
Takeuchi K, Ichinohe M, Sekiguchi A., J. Am. Chem. Soc. 133(32), 2011
PMID: 21776998
Takeuchi K, Ichinohe M, Sekiguchi A., J. Am. Chem. Soc. 133(32), 2011
PMID: 21776998
AUTHOR UNKNOWN, 0
Stable heterocyclopentane-1,3-diyls.
Hinz A, Schulz A, Villinger A., Angew. Chem. Int. Ed. Engl. 54(9), 2015
PMID: 25604347
Hinz A, Schulz A, Villinger A., Angew. Chem. Int. Ed. Engl. 54(9), 2015
PMID: 25604347
AUTHOR UNKNOWN, Angew. Chem. 127(), 2015
Activation of small molecules by phosphorus biradicaloids.
Hinz A, Kuzora R, Rosenthal U, Schulz A, Villinger A., Chemistry 20(45), 2014
PMID: 25266101
Hinz A, Kuzora R, Rosenthal U, Schulz A, Villinger A., Chemistry 20(45), 2014
PMID: 25266101
[P(μ-NTer)]2: a biradicaloid that is stable at high temperature.
Beweries T, Kuzora R, Rosenthal U, Schulz A, Villinger A., Angew. Chem. Int. Ed. Engl. 50(38), 2011
PMID: 21858902
Beweries T, Kuzora R, Rosenthal U, Schulz A, Villinger A., Angew. Chem. Int. Ed. Engl. 50(38), 2011
PMID: 21858902
AUTHOR UNKNOWN, Angew. Chem. 123(), 2011
Small inorganic rings in the 21st century: from fleeting intermediates to novel isolable entities.
He G, Shynkaruk O, Lui MW, Rivard E., Chem. Rev. 114(16), 2014
PMID: 24605824
He G, Shynkaruk O, Lui MW, Rivard E., Chem. Rev. 114(16), 2014
PMID: 24605824
AUTHOR UNKNOWN, 0
(L)2 C2 P2 : Dicarbondiphosphide Stabilized by N-Heterocyclic Carbenes or Cyclic Diamido Carbenes.
Li Z, Chen X, Andrada DM, Frenking G, Benko Z, Li Y, Harmer JR, Su CY, Grutzmacher H., Angew. Chem. Int. Ed. Engl. 56(21), 2017
PMID: 28436079
Li Z, Chen X, Andrada DM, Frenking G, Benko Z, Li Y, Harmer JR, Su CY, Grutzmacher H., Angew. Chem. Int. Ed. Engl. 56(21), 2017
PMID: 28436079
AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 129(), 2017
Carbon-based two electron σ-donor ligands beyond classical N-heterocyclic carbenes.
Ghadwal RS., Dalton Trans 45(41), 2016
PMID: 27427200
Ghadwal RS., Dalton Trans 45(41), 2016
PMID: 27427200
Facile access to silyl-functionalized N-heterocyclic olefins with HSiCl3.
Ghadwal RS, Reichmann SO, Engelhardt F, Andrada DM, Frenking G., Chem. Commun. (Camb.) 49(82), 2013
PMID: 24005446
Ghadwal RS, Reichmann SO, Engelhardt F, Andrada DM, Frenking G., Chem. Commun. (Camb.) 49(82), 2013
PMID: 24005446
AUTHOR UNKNOWN, 0
Structurally versatile phosphine and amine donors constructed from N-heterocyclic olefin units.
Paisley NR, Lui MW, McDonald R, Ferguson MJ, Rivard E., Dalton Trans 45(24), 2016
PMID: 26924395
Paisley NR, Lui MW, McDonald R, Ferguson MJ, Rivard E., Dalton Trans 45(24), 2016
PMID: 26924395
Using N-Heterocyclic Vinyl Ligands to Access Stable Divinylgermylenes and a Germylium Cation.
Hering-Junghans C, Andreiuk P, Ferguson MJ, McDonald R, Rivard E., Angew. Chem. Int. Ed. Engl. 56(22), 2016
PMID: 28510351
Hering-Junghans C, Andreiuk P, Ferguson MJ, McDonald R, Rivard E., Angew. Chem. Int. Ed. Engl. 56(22), 2016
PMID: 28510351
Bis(N-heterocyclic olefin) Derivative: An Efficient Precursor for Isophosphindolylium Species.
Chong CC, Rao B, Ganguly R, Li Y, Kinjo R., Inorg Chem 56(15), 2017
PMID: 28135074
Chong CC, Rao B, Ganguly R, Li Y, Kinjo R., Inorg Chem 56(15), 2017
PMID: 28135074
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Mono- and di-cationic hydrido boron compounds.
Ghadwal RS, Schurmann CJ, Andrada DM, Frenking G., Dalton Trans 44(32), 2015
PMID: 26200103
Ghadwal RS, Schurmann CJ, Andrada DM, Frenking G., Dalton Trans 44(32), 2015
PMID: 26200103
Ghadwal, Eur. J. Inorg. Chem. (), 2014
Facile routes to abnormal-NHC-cobalt(ii) complexes.
Ghadwal RS, Lamm JH, Rottschafer D, Schurmann CJ, Demeshko S., Dalton Trans 46(24), 2017
PMID: 28573296
Ghadwal RS, Lamm JH, Rottschafer D, Schurmann CJ, Demeshko S., Dalton Trans 46(24), 2017
PMID: 28573296
Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex.
Ghadwal RS, Rottschafer D, Andrada DM, Frenking G, Schurmann CJ, Stammler HG., Dalton Trans 46(24), 2017
PMID: 28590484
Ghadwal RS, Rottschafer D, Andrada DM, Frenking G, Schurmann CJ, Stammler HG., Dalton Trans 46(24), 2017
PMID: 28590484
AUTHOR UNKNOWN, 0
Schmidpeter, Chem. Ber. 128(), 1995
Schrödel, Angew. Chem. Int. Ed. Engl. 34(), 1995
AUTHOR UNKNOWN, Angew. Chem. 107(), 1995
Jochem, Angew. Chem. Int. Ed. Engl. 33(), 1994
AUTHOR UNKNOWN, Angew. Chem. 106(), 1994
Schrödel, Chem. Ber. 130(), 1997
Schrödel, Z. Naturforsch. B: Chem. Sci. 51(), 1996
Jochem, Chem. Eur. J. 2(), 1996
Schmidpeter, Angew. Chem. Int. Ed. Engl. 30(), 1991
AUTHOR UNKNOWN, Angew. Chem. 103(), 1991
AUTHOR UNKNOWN, 0
Jochem, Angew. Chem. 106(), 1994
AUTHOR UNKNOWN, 0
Intercepting low oxidation state main group hydrides with a nucleophilic N-heterocyclic olefin.
Al-Rafia SM, Malcolm AC, Liew SK, Ferguson MJ, McDonald R, Rivard E., Chem. Commun. (Camb.) 47(24), 2011
PMID: 21562648
Al-Rafia SM, Malcolm AC, Liew SK, Ferguson MJ, McDonald R, Rivard E., Chem. Commun. (Camb.) 47(24), 2011
PMID: 21562648
Allen, J. Chem. Soc. Perkin Trans. 2 (), 1987
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Teil dieser Dissertation
Stabilisierung subvalenter Kohlenstoff- und Phosphorverbindungen mittels unkonventioneller Kohlenstoff-Donorliganden
Rottschäfer D (2020)
Bielefeld: Universität Bielefeld.
Rottschäfer D (2020)
Bielefeld: Universität Bielefeld.
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