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

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• 作者：Nikolay T. Tzvetkov ; Prashant A. Waske ; Beate Neumann ; Hans-Georg Stammler ; Jochen Mattay
• 关键词：Organogel ; Triazine ; Pyrrolidine ; Self-assembly
• 刊名：Tetrahedron Letters
• 出版年：2008
• 出版时间：3 March 2008
• 年：2008
• 卷：49
• 期：10
• 页码：1710-1713
• 全文大小：202 K

文摘

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 δ-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 α-alkylated 2-oxocyclopentanecarboxylate derivatives does not lead to any cyclization products via a δ-hydrogen abstraction process. In this case α-C–C bond cleavage as a predominant process was observed.