Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions

Waske PA, Mattay J (2005)
TETRAHEDRON 61(43): 10321-10330.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Various ring-fused cyclopropyl silyl ethers with an benzylic, olefinic or acetylenic side chain have been synthesized. Upon oxidative photoinduced electron transfer (PET) the cyclopropane ring opens and forms a reactive beta-keto radical, which undergoes intramolecular cyclization. In some cases we observed only formation of ring opened non-cyclized products. With olefinic side chain 5-exo-trig mode of cyclization rather than 6-endo-trig mode of cyclization takes place whereas in case of acetylenic side chain we observed 6-endo cyclization. (c) 2005 Elsevier Ltd. All rights reserved.
Stichworte
siloxy cyclopropanes; electron transfer; polycycles; radical ions; radical reactions; domino reactions
Erscheinungsjahr
2005
Zeitschriftentitel
TETRAHEDRON
Band
61
Ausgabe
43
Seite(n)
10321-10330
ISSN
0040-4020
Page URI
https://pub.uni-bielefeld.de/record/1602028

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Waske PA, Mattay J. Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions. TETRAHEDRON. 2005;61(43):10321-10330.
Waske, P. A., & Mattay, J. (2005). Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions. TETRAHEDRON, 61(43), 10321-10330. doi:10.1016/j.tet.2005.08.034
Waske, P. A., and Mattay, J. (2005). Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions. TETRAHEDRON 61, 10321-10330.
Waske, P.A., & Mattay, J., 2005. Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions. TETRAHEDRON, 61(43), p 10321-10330.
P.A. Waske and J. Mattay, “Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions”, TETRAHEDRON, vol. 61, 2005, pp. 10321-10330.
Waske, P.A., Mattay, J.: Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions. TETRAHEDRON. 61, 10321-10330 (2005).
Waske, PA, and Mattay, Jochen. “Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions”. TETRAHEDRON 61.43 (2005): 10321-10330.