Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones

Kirschberg T, Mattay J (1996)
The Journal of Organic Chemistry 61(25): 8885-8896.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Reductive photoinduced electron transfer (PET) reactions have been performed with various bicyclic alpha-cyclopropyl-substituted ketones and tertiary amines. The reaction resulted in a regioselective cleavage of one cyclopropyl bond under formation of an exocyclic radical with an endocyclic enolate unit. In the case of bicyclic ketones with an unsaturated side chain, various bicyclic, spirocyclic, and tricyclic products are accessible via radical cyclization, depending on the position of the alkenyl substituent. In addition to triethylamine, N-silylated amines have also been used as electron donors, leading to a variety of compounds, among them are silylated fragmentation products, indicating that a proton is transferred from not only the amine radical cation but also the cationic silyl group. The intramolecular Paterno-Buchi reaction has also been studied for cyclopropane derivatives of the jasmone type leading to tetracyclic oxetanes. Finally, alpha-epoxy-substituted ketones have been investigated under PET conditions, yielding ring-opened products.
Erscheinungsjahr
Zeitschriftentitel
The Journal of Organic Chemistry
Band
61
Zeitschriftennummer
25
Seite
8885-8896
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eISSN
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Kirschberg T, Mattay J. Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones. The Journal of Organic Chemistry. 1996;61(25):8885-8896.
Kirschberg, T., & Mattay, J. (1996). Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones. The Journal of Organic Chemistry, 61(25), 8885-8896. doi:10.1021/jo961015b
Kirschberg, T., and Mattay, J. (1996). Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones. The Journal of Organic Chemistry 61, 8885-8896.
Kirschberg, T., & Mattay, J., 1996. Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones. The Journal of Organic Chemistry, 61(25), p 8885-8896.
T. Kirschberg and J. Mattay, “Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones”, The Journal of Organic Chemistry, vol. 61, 1996, pp. 8885-8896.
Kirschberg, T., Mattay, J.: Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones. The Journal of Organic Chemistry. 61, 8885-8896 (1996).
Kirschberg, T, and Mattay, Jochen. “Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones”. The Journal of Organic Chemistry 61.25 (1996): 8885-8896.

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