Synthetic applications in radical/radical cationic cascade reactions

Rinderhagen H, Mattay J (2004)
CHEMISTRY-A EUROPEAN JOURNAL 10(4): 851-874.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Oxidative photoinduced electron transfer (PET) reactions have been performed with various cyclic cyclopropyl(vinyl) silyl ethers bearing an olefinic or acetylenic side chain. The reactions result in bi- to tetracyclic ring systems via a fragmentation-radical/ radical cationic addition reaction pathway with well defined ring juncture. The mode of cyclisation (endo/exo) can be partially controlled by addition of nucleophiles due to the suppression of radical cationic reaction pathways. Quantum chemical calculation of the cyclisation transition states underline the experimentally found selectivities. Additional mechanistic studies concerning the saturation step reveal that the final radical is saturated mostly by the solvent and traces of water in the solvent.
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CHEMISTRY-A EUROPEAN JOURNAL
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10
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4
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851-874
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Rinderhagen H, Mattay J. Synthetic applications in radical/radical cationic cascade reactions. CHEMISTRY-A EUROPEAN JOURNAL. 2004;10(4):851-874.
Rinderhagen, H., & Mattay, J. (2004). Synthetic applications in radical/radical cationic cascade reactions. CHEMISTRY-A EUROPEAN JOURNAL, 10(4), 851-874. doi:10.1002/chem.200304827
Rinderhagen, H., and Mattay, J. (2004). Synthetic applications in radical/radical cationic cascade reactions. CHEMISTRY-A EUROPEAN JOURNAL 10, 851-874.
Rinderhagen, H., & Mattay, J., 2004. Synthetic applications in radical/radical cationic cascade reactions. CHEMISTRY-A EUROPEAN JOURNAL, 10(4), p 851-874.
H. Rinderhagen and J. Mattay, “Synthetic applications in radical/radical cationic cascade reactions”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 10, 2004, pp. 851-874.
Rinderhagen, H., Mattay, J.: Synthetic applications in radical/radical cationic cascade reactions. CHEMISTRY-A EUROPEAN JOURNAL. 10, 851-874 (2004).
Rinderhagen, H, and Mattay, Jochen. “Synthetic applications in radical/radical cationic cascade reactions”. CHEMISTRY-A EUROPEAN JOURNAL 10.4 (2004): 851-874.

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Daten bereitgestellt von Europe PubMed Central.

Regioselective oxidative ring opening of cyclopropyl silyl ethers: a quantum chemical study.
Rinderhagen H, Mattay J, Nussbaum R, Bally T., Chemistry 16(24), 2010
PMID: 20458710

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