Nucleophilic substitution of α-halo-ketones. XXIII. Acetolysis of 1-chloro-3-phenoxy-1-phenylthio-2-propanones. An intramolecular trans-acetylation involving phenoxide anion as the leaving group |
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| Authors: | Alba Pusino Antonio Saba Vittorio Rosnati |
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| Institution: | Istituto di Chimica Organica, Universia`di Sassari, Via Vienna 2, I-07100 Sassari Italy;Department of Chemical Sciences and Technologies, II University of Rome, Via O. Raimondo, I-00173 Rome Italy |
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| Abstract: | The acetolyses of α-chloro-ketones1a-c,2a-c,9a and11a have been investigated parallely. Several aspects of the mechanisms involved in chlorine normal and cine substitution have been elucidated. Intramolecular trans-acetylation, ultimately leading to fragmentation of acetoxy-ketones3b,4a and4c, have been postulated to account for the formation of thiol ester6, aldehyde5a and ketone5c, respectively. |
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