Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: dependence of the regioselectivity on alcohol addition and pressure effects

Ackermann L, Heidbreder A, Wurche F, Klarner FG, Mattay J (1999)
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 (4): 863-870.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Unsaturated silyl enol ethers are irradiated in the presence of electron transfer sensitizers. The efficiency of the cyclization reaction using different sensitizers is investigated. The endolexo regiochemistry of the ring closure reaction can either be controlled by variation of the silyl group or by addition of alcohol. Furthermore, a dependence of the regiochemistry on pressure is revealed and it seems that it can be related to acetonitrile acting as a nucleophile at 1500 bar. As key intermediates radical cations and radicals are involved.
Erscheinungsjahr
Zeitschriftentitel
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Zeitschriftennummer
4
Seite
863-870
ISSN
eISSN
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Ackermann L, Heidbreder A, Wurche F, Klarner FG, Mattay J. Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: dependence of the regioselectivity on alcohol addition and pressure effects. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2. 1999;(4):863-870.
Ackermann, L., Heidbreder, A., Wurche, F., Klarner, F. G., & Mattay, J. (1999). Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: dependence of the regioselectivity on alcohol addition and pressure effects. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(4), 863-870. doi:10.1039/a807683i
Ackermann, L., Heidbreder, A., Wurche, F., Klarner, F. G., and Mattay, J. (1999). Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: dependence of the regioselectivity on alcohol addition and pressure effects. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 863-870.
Ackermann, L., et al., 1999. Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: dependence of the regioselectivity on alcohol addition and pressure effects. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, (4), p 863-870.
L. Ackermann, et al., “Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: dependence of the regioselectivity on alcohol addition and pressure effects”, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, pp. 863-870.
Ackermann, L., Heidbreder, A., Wurche, F., Klarner, F.G., Mattay, J.: Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: dependence of the regioselectivity on alcohol addition and pressure effects. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2. 863-870 (1999).
Ackermann, L, Heidbreder, A, Wurche, F, Klarner, FG, and Mattay, Jochen. “Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers: dependence of the regioselectivity on alcohol addition and pressure effects”. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 4 (1999): 863-870.