Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study
Rinderhagen H, Mattay J, Nussbaum R, Bally T (2010)
CHEMISTRY-A EUROPEAN JOURNAL 16(24): 7121-7124.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
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Autor*in
Rinderhagen, Heiko;
Mattay, JochenUniBi;
Nussbaum, Rafael;
Bally, Thomas
Einrichtung
Abstract / Bemerkung
In contrast to the structurally and configurationally stable alkyl- or aryl-substituted cyclopropyl radical cations, cyclopropyl silyl ethers undergo spontaneous ring opening upon oxidation whereby the endocyclic C-C(OTMS) bond is cleaved with remarkable selectivity. DFT calculations on 1-trimethylsilyloxybicyclo[4.1.0]heptane show that this selectivity arises from the topology of the potential surface of the corresponding radical cation which is initially generated in a very steep region of the potential surface from where the steepest descent leads to cleavage of the endocyclic rather than the lateral C C(OTMS) bond. Cleavage of the lateral bond leads to interesting conformational changes which are explored in detail.
Stichworte
cations;
electron transfer;
radicals;
potential;
surfaces;
cyclopropyl ethers
Erscheinungsjahr
2010
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
16
Ausgabe
24
Seite(n)
7121-7124
ISSN
0947-6539
Page URI
https://pub.uni-bielefeld.de/record/1794970
Zitieren
Rinderhagen H, Mattay J, Nussbaum R, Bally T. Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study. CHEMISTRY-A EUROPEAN JOURNAL. 2010;16(24):7121-7124.
Rinderhagen, H., Mattay, J., Nussbaum, R., & Bally, T. (2010). Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study. CHEMISTRY-A EUROPEAN JOURNAL, 16(24), 7121-7124. https://doi.org/10.1002/chem.201000255
Rinderhagen, Heiko, Mattay, Jochen, Nussbaum, Rafael, and Bally, Thomas. 2010. “Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study”. CHEMISTRY-A EUROPEAN JOURNAL 16 (24): 7121-7124.
Rinderhagen, H., Mattay, J., Nussbaum, R., and Bally, T. (2010). Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study. CHEMISTRY-A EUROPEAN JOURNAL 16, 7121-7124.
Rinderhagen, H., et al., 2010. Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study. CHEMISTRY-A EUROPEAN JOURNAL, 16(24), p 7121-7124.
H. Rinderhagen, et al., “Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 16, 2010, pp. 7121-7124.
Rinderhagen, H., Mattay, J., Nussbaum, R., Bally, T.: Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study. CHEMISTRY-A EUROPEAN JOURNAL. 16, 7121-7124 (2010).
Rinderhagen, Heiko, Mattay, Jochen, Nussbaum, Rafael, and Bally, Thomas. “Regioselective Oxidative Ring Opening of Cyclopropyl Silyl Ethers: A Quantum Chemical Study”. CHEMISTRY-A EUROPEAN JOURNAL 16.24 (2010): 7121-7124.
1 Zitation in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Recent advances in the synthesis of functionalised monofluorinated compounds.
Fustero S, Sedgwick DM, Román R, Barrio P., Chem Commun (Camb) 54(70), 2018
PMID: 30066002
Fustero S, Sedgwick DM, Román R, Barrio P., Chem Commun (Camb) 54(70), 2018
PMID: 30066002
24 References
Daten bereitgestellt von Europe PubMed Central.
Roth, J. Am. Chem. Soc. 102(), 1980
Roth, J. Am. Chem. Soc. 103(), 1981
Roth, J. Am. Chem. Soc. 105(), 1983
Roth, Can. J. Chem. 61(), 1983
Roth, J. Phys. Chem. A 103(), 1999
Krogh-Jespersen, J. Am. Chem. Soc. 114(), 1992
Herbertz, J. Am. Chem. Soc. 120(), 1998
Wong, Tetrahedron Lett. 20(), 1979
Hudson, J. Org. Chem. 58(), 1993
Karki, J. Am. Chem. Soc. 119(), 1997
Dinnocenzo, J. Am. Chem. Soc. 115(), 1993
Dinnocenzo, J. Am. Chem. Soc. 112(), 1990
Dinnocenzo, J. Am. Chem. Soc. 119(), 1997
Dinnocenzo, J. Am. Chem. Soc. 119(), 1997
Roth, 2001
Synthetic applications in radical/radical cationic cascade reactions.
Rinderhagen H, Mattay J., Chemistry 10(4), 2004
PMID: 14978812
Rinderhagen H, Mattay J., Chemistry 10(4), 2004
PMID: 14978812
AUTHOR UNKNOWN, 0
Rinderhagen, J. Inf. Rec. Mater. (), 1998
Rinderhagen, J. Inf. Rec. Mater. (), 2000
Rinderhagen, Tetrahedron 62(), 2006
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
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