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
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, 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

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