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.

Journal Article | Published | English

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Abstract
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.
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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.
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.
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PMID: 20458710
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