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Phosphahelicenes with (Thio)Phosphinic Acid and Ester Functions by the Oxidative Photocyclisation Approach |
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| Authors: | Julie Febvay Dr. Charles S. Demmer Dr. Pascal Retailleau Dr. Jeanne Crassous Dr. Laura Abella Prof. Jochen Autschbach Dr. Arnaud Voituriez Dr. Angela Marinetti |
| Affiliation: | 1. Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France;2. Institut des Sciences Chimiques de Rennes UMR CNRS 6226, Univ Rennes, Campus de Beaulieu, 35042 Rennes Cedex, France;3. Department of Chemistry, University at Buffalo, State University of New York, Buffalo, NY, 14260-3000 USA |
| Abstract: | Phosphahelicenes with thiophosphinic acid and ester functions have been obtained by the oxidative photocyclisation of olefins bearing both a benzophenanthrene and a benzophosphole unit. When the method has been extended to olefins bearing a partially saturated benzophospholene unit, a divergent regioselectivity of the photocyclisation step has been observed, leading to new helicenes in which the phosphorus function is located on the external rim of the helical backbone. The observed regioselectivity correlates well with the free-valence numbers of the atoms involved in the photocyclisation reaction (DFT calculations). |
| Keywords: | phosphahelicenes phospholenes photocyclization p-stereogenic thiophosphinic acids |