Abstract
N-Heterocyclic germylenes are known to exist in two structurally different forms, the planar Meller germylenes and the monoimino germylenes that feature an envelope structure. This essay reviews recent reports dealing with radical and cationic Meller type germylenes featuring the monoimino germylene structure, discusses their transformations and relationships, and asks the question whether indeed N-heterocyclic germylenes can be turned into Lewis acids.
Similar content being viewed by others
References
A. Meller, C.-P. Gräbe, Chem. Ber. 118, 2020 (1985).
J. Pfeiffer, M. Noltemeyer, A. Meller, Z. Anorg. Chem. 572, 145 (1989).
for recent reviews on NHC see: a) V. Cesar, S. Bellemin-Laponnaz, L. H. Gade, Chem. Soc. Rev. 35, 619 (2004); b) J. A. Mata, M. Poyatos, E. Peris, Coord. Chem. Rev. 251, 841 (2007); c) R. E. Douthwaite, Coord. Chem. Rev. 251, 702 (2007); d) D. Pugh, A. A. Danopoulos, Coord. Chem. Rev. 251, 610 (2007); e) O. Kühl, Chem. Soc. Rev. 36, 592 (2007)
D. Nemcsok, K. Wichmann, G. Frenking, Organometallics 3, 3640 (2004).
J. Olah, F. De Proft, T. Veszpremi, P. Geerlings, J. Phys. Chem. A 109, 1608 (2005).
for a recent review of NHGe see: O. Kühl, Coord. Chem. Rev. 248, 411 (2004).
W. A. Herrmann, M. Denk, J. Behm, W. Scherer, F.-R. Klingan, H. Bock, B. Solouki, M. Wagner, Angew. Chem. 104, 1489 (1992).
O. Kühl, P. Lönnecke, J. Heinicke, Inorg. Chem. 42, 2836 (2003).
B. Gehrhus, P. B. Hitchcock, M. F. Lappert, J. Chem. Soc., Dalton Trans. 3094 (2000)
H. Braunschweig, B. Gehrhus, P. B. Hitchcock, M. F. Lappert, Z. Anorg. Allg. Chem. 621, 1922 (1995).
B. Gehrhus, P. B. Hitchcock, M. F. Lappert, J. Heinicke, R. Boese, D. Bläser, J. Organomet. Chem. 521, 211 (1996).
The annelation effect describes the influence of the anellated ring system (benza, pyrido, naphtha etc) on the saturated N-heterocyclic germylene represented by structure 1; J. Heinicke, A. Oprea, M. K. Kindermann, T. Karpati, L. Nyulaszi, T. Veszpremi, Chem. Eur. J. 4, 541 (1998)
O. Kühl, P. Lönnecke, J. Heinicke, Polyhedron 20, 2215 (2001).
L. Pause, M. Robert, J. Heinicke, O. Kühl, Perkin Trans. 2, 1383 (2001).
J. Heinicke, A. Oprea, Heteroatom. Chem. 9, 439 (1998).
O. Kühl, K. Lifson, W. Langel, Eur. J. Org. Chem. 2336 (2006)
S. R. Foley, C. Bensimon, D. S. Richeson, J. Am. Chem. Soc. 119, 10359 (1997).
H. V. R. Dias, Z. Wang, W. Jin, Coord. Chem. Rev. 176, 67 (1998).
A. Akari, J. J. Byrne, I. Saur, G. Rima, H. Gornitzka, J. Barrau, J. Organomet. Chem. 622, 190 (2001).
I. Saur, S. Garcia Alonso, J. Barrau, Appl. Organomet. Chem. 19, 414 (2005)
O. Kühl, P. Lönnecke, J. Heinicke, New J. Chem. 26, 1304 (2002).
C. Heinemann, W. A. Herrmann, W. Thiel, J. Organomet. Chem. 475, 73 (1994).
R. West, D. F. Moser, I. A. Guzei, G.-W. Lee, A. Naka, W. Li, A. Zabulla, S. Bukalov, L. Leites, Organometallics 25, 2709 (2006).
I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, N. M. Khvoinova, A. Y. Baurin, S. Dechert, M. Hummert, H. Schumann, Organometallics 23, 3714 (2004).
I. L. Fedushkin, N. M. Khvoinova, A. Y. Baurin, G. K. Fukin, V. K. Cherkasov, M. P. Bubnov, Inorg. Chem. 43, 7807 (2004).
B. Turmanskij, P. Pine, Y. Apeloig, N. J. Hill, R. West, J. Am. Chem. Soc. 125, 7786 (2004).
G. A. Abakumov, V. K. Cherkasov, A. V. Piskunov, L. A. Aivaz’yan, N. O. Druzhkov, Dokl. Chem. 404, 189 (2005).
G. A. Abakumov, V. K. Cherkasov, A. V. Piskunov, N. O. Druzhkov, Dokl. Chem. 399, 223 (2004).
S. Hauptmann, Organische Chemie; Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985
A. Hollemann, N. Wiberg, Lehrbuch der Anorganischen Chemie, 91st-100th Edition, Walter de Gruyter, New York, Berlin, 1985
Y. Ding, Q. Ma, H. W. Roesky, I. Uson, M. Noltemeyer, H.-G. Schmidt, Dalton Trans. 1094 (2003)
A. E. Ayers, T. M. Klapötke, H. V. R. Dias, Inorg. Chem. 40, 1000 (2001).
Y. Ding, H. W. Roesky, M. Noltemeyer, H.-G. Schmidt, P. P. Power, Organometallics 20, 1190 (2001)
I. Saur, K. Miqueu, G. Rima, J. Barrau, V. Lemierre, A. Chrostowska, J.-M. Sotiropoulos, G. Pfister-Guillouzo, Organometallics 22, 3143 (2003).
I. Saur, G. Rima, K. Miqueu, H. Gornitzka, J. Barrau, J. Organomet. Chem. 672, 77 (2003)
L. W. Pineda, V. Jancik, H. W. Roesky, D. Neculai, A. M. Neculai, Angew. Chem. Int. Ed. 43, 1419 (2004)
L. W. Pineda, V. Jancik, H. W. Roesky, R. Herbst-Irmer, Angew. Chem. Int. Ed. 43, 5534 (2004).
Y. Ding, Q. Ma, H. W. Roesky, R. Herbst-Irmer, I. Uson, M. Noltemeyer, H.-G. Schmidt, Organometallics 21, 5216 (2002).
M. Stender, A. D. Phillips, P. P. Power, Inorg. Chem. 40, 5314 (2001).
Y. Ding, H. Hao, H.W. Roesky, M. Noltemeyer, H.-G. Schmidt, Organometallics 20, 4806 (2001).
I. Saur, G. Rima, H. Gornitzka, K. Miqueu, J. Barrau, Organometallics 22, 1106 (2003).
Y. Ding, Q. Ma, I. Uson, H. W. Roesky, M. Noltemeyer, H.-G. Schmidt, J. Am. Chem. Soc. 124, 8542 (2002).
a) P. A. Rupar, M. C. Jennings, P. J. Ragogna, K. M. Baines, Organometallics 26, 4109 (2007).; b) P. A. Rupar, V. N. Staroverov, P. J. Ragogna, K. M. Baines, J. Am. Chem. Soc. 129, 15138 (2007)
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Kühl, O. Can N-heterocyclic germylenes behave as Lewis acids - is there another side to Meller germylenes?. cent.eur.j.chem. 6, 365–372 (2008). https://doi.org/10.2478/s11532-008-0040-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11532-008-0040-5