Benzyl (phenyl) gamma- and delta-lactones via photoinduced tandem Ar-C, C-O bond formation |
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| Authors: | Protti Stefano Fagnoni Maurizio Albini Angelo |
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| Institution: | Department of Organic Chemistry, The University, V. Taramelli 10, 27100 Pavia, Italy. |
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| Abstract: | A convenient metal-free procedure for the preparation of benzyl (phenyl) gamma- and delta-lactones is illustrated. This method is based on the photochemical generation of phenyl cations and their reaction with 3, 4, or 5-alkenoic acids. This leads to a phenyl- or benzyl-substituted lactone by tandem formation of an aryl-C and C-O bond. The intermediacy of a phenonium ion imparts a full regio- and stereoselectivity to the reaction. |
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