Synthetic applications in radical/radical cationic cascade reactions

Rinderhagen, H; Mattay, Jochen

Synthetic applications in radical/radical cationic cascade reactions

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

Zeitschriftenaufsatz | Veröffentlicht | Englisch

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DOI

https://doi.org/10.1002/chem.200304827

Autor*in

Rinderhagen, H; Mattay, Jochen^UniBi

Einrichtung

Fakultät für Chemie > Industrielle Organische Chemie und Biotechnologie

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.

Stichworte

radical; polycycles; radical ions; domino reactions; electron transfer; reactions

Erscheinungsjahr

2004

Zeitschriftentitel

CHEMISTRY-A EUROPEAN JOURNAL

Band

Ausgabe

Seite(n)

851-874

ISSN

0947-6539

eISSN

1521-3765

Page URI

https://pub.uni-bielefeld.de/record/1608568

Zitieren

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. https://doi.org/10.1002/chem.200304827

Rinderhagen, H, and Mattay, Jochen. 2004. “Synthetic applications in radical/radical cationic cascade reactions”. CHEMISTRY-A EUROPEAN JOURNAL 10 (4): 851-874.

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.