Photoinduced radical reactions of alpha-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: alpha-cleavage and cyclization to the skeleton of linear cyclohexano diquinanes

Tzvetkov NT, Waske PA, Neumann B, Stammler H-G, Mattay J (2008)
TETRAHEDRON LETTERS 49(10): 1710-1713.

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Abstract
The tricyclic core of linear cyclohexano diquinanes was synthesized using photoinduced electron transfer (PET) as a key step. The reaction proceeded in high regioselective manner via ketyl radical anions leading to distonic delta-keto radical anion as reactive intermediates. The irradiation was carried out at a wavelength of 254 nm with triethylamine (TEA) as a strong reducing reagent in acetonitrile. We also showed that the photolysis of the alpha-alkylated 2-oxocyclopentanecarboxylate derivatives does not lead to any cyclization products via a delta-hydrogen abstraction process. In this case alpha-C-C bond cleavage as a predominant process was observed. (c) 2007 Elsevier Ltd. All rights reserved.
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Tzvetkov NT, Waske PA, Neumann B, Stammler H-G, Mattay J. Photoinduced radical reactions of alpha-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: alpha-cleavage and cyclization to the skeleton of linear cyclohexano diquinanes. TETRAHEDRON LETTERS. 2008;49(10):1710-1713.
Tzvetkov, N. T., Waske, P. A., Neumann, B., Stammler, H. - G., & Mattay, J. (2008). Photoinduced radical reactions of alpha-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: alpha-cleavage and cyclization to the skeleton of linear cyclohexano diquinanes. TETRAHEDRON LETTERS, 49(10), 1710-1713.
Tzvetkov, N. T., Waske, P. A., Neumann, B., Stammler, H. - G., and Mattay, J. (2008). Photoinduced radical reactions of alpha-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: alpha-cleavage and cyclization to the skeleton of linear cyclohexano diquinanes. TETRAHEDRON LETTERS 49, 1710-1713.
Tzvetkov, N.T., et al., 2008. Photoinduced radical reactions of alpha-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: alpha-cleavage and cyclization to the skeleton of linear cyclohexano diquinanes. TETRAHEDRON LETTERS, 49(10), p 1710-1713.
N.T. Tzvetkov, et al., “Photoinduced radical reactions of alpha-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: alpha-cleavage and cyclization to the skeleton of linear cyclohexano diquinanes”, TETRAHEDRON LETTERS, vol. 49, 2008, pp. 1710-1713.
Tzvetkov, N.T., Waske, P.A., Neumann, B., Stammler, H.-G., Mattay, J.: Photoinduced radical reactions of alpha-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: alpha-cleavage and cyclization to the skeleton of linear cyclohexano diquinanes. TETRAHEDRON LETTERS. 49, 1710-1713 (2008).
Tzvetkov, Nikolay T., Waske, Prashant A., Neumann, Beate, Stammler, Hans-Georg, and Mattay, Jochen. “Photoinduced radical reactions of alpha-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: alpha-cleavage and cyclization to the skeleton of linear cyclohexano diquinanes”. TETRAHEDRON LETTERS 49.10 (2008): 1710-1713.
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