Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to beta-keto radicals

Rinderhagen H, Waske PA, Mattay J (2006)
TETRAHEDRON 62(27): 6589-6593.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor/in
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Abstract / Bemerkung
Siloxy cyclopropanes undergo ring opening and fragmentation of formal silyl cations under formation of beta-keto radicals. These reactive intermediates can be used in inter- and intramolecular addition reactions leading to complex ring systems if more than one unsaturated side chain is present in the starting material. Beside some synthetic examples mainly the mechanism will be discussed focusing on the structure of the primarily formed radical cations, the regioselectivity of cyclopropane cleavage (endo vs exo ring opening). leaving of the silyl group, and termination by H-transfer. (c) 2006 Elsevier Ltd. All rights reserved.
Stichworte
siloxy cyclopropanes; radical cations; radicals; radical cascade reactions; reaction mechanism; photoinduced electron transfer
Erscheinungsjahr
2006
Zeitschriftentitel
TETRAHEDRON
Band
62
Ausgabe
27
Seite(n)
6589-6593
ISSN
0040-4020
Page URI
https://pub.uni-bielefeld.de/record/1598861

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Rinderhagen H, Waske PA, Mattay J. Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to beta-keto radicals. TETRAHEDRON. 2006;62(27):6589-6593.
Rinderhagen, H., Waske, P. A., & Mattay, J. (2006). Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to beta-keto radicals. TETRAHEDRON, 62(27), 6589-6593. doi:10.1016/j.tet.2006.03.060
Rinderhagen, H., Waske, P. A., and Mattay, J. (2006). Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to beta-keto radicals. TETRAHEDRON 62, 6589-6593.
Rinderhagen, H., Waske, P.A., & Mattay, J., 2006. Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to beta-keto radicals. TETRAHEDRON, 62(27), p 6589-6593.
H. Rinderhagen, P.A. Waske, and J. Mattay, “Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to beta-keto radicals”, TETRAHEDRON, vol. 62, 2006, pp. 6589-6593.
Rinderhagen, H., Waske, P.A., Mattay, J.: Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to beta-keto radicals. TETRAHEDRON. 62, 6589-6593 (2006).
Rinderhagen, H, Waske, PA, and Mattay, Jochen. “Facile ring opening of siloxy cyclopropanes by photoinduced electron transfer. A new way to beta-keto radicals”. TETRAHEDRON 62.27 (2006): 6589-6593.