Artículo
Experimental and Theoretical Analysis of the Thiol-Promoted Fragmentation of 2-Halo-3-tosyl-oxanorbornadienes
Autor/es | Carranza César, Marina
Carmona Asenjo, Ana Teresa Navo, Claudio D. Robina Ramírez, Inmaculada Fratta, Simone Newburn, Carlos Jimenez-Oses, Gonzalo Moreno Vargas, Antonio José |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2023 |
Fecha de depósito | 2023-11-07 |
Publicado en |
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Resumen | 2-Halo-3-tosyl-oxanorbornadienes are able to accept two thiol molecules through an initial nucleophilic substitution, giving isolable oxabicyclic thiovinyl sulfones that, subsequently, can react with a second thiol molecule ... 2-Halo-3-tosyl-oxanorbornadienes are able to accept two thiol molecules through an initial nucleophilic substitution, giving isolable oxabicyclic thiovinyl sulfones that, subsequently, can react with a second thiol molecule via thio-Michael addition. The resulting oxanorbornenic thioketals undergo retro-Diels-Alder (rDA) fragmentation to release a furan derivative and a ketene S,S-acetal. The substitution pattern of the oxanorbornadienic skeleton influences the rate of the rDA through electronic and steric factors examined by quantum mechanical calculations. |
Agencias financiadoras | Ministerio de Ciencia e Innovación (MICIN). España Junta de Andalucía European Union (UE) |
Identificador del proyecto | PID2020-116460RB-100
PID2021- 125946OB-I00 CEX2021-001136-S P20_00532 671881 |
Cita | Carranza César, M., Carmona Asenjo, A.T., Navo, C.D., Robina Ramírez, I., Fratta, S., Newburn, C.,...,Moreno Vargas, A.J. (2023). Experimental and Theoretical Analysis of the Thiol-Promoted Fragmentation of 2-Halo-3-tosyl-oxanorbornadienes. Organic Letters, 25 (41), 7481-7485. https://doi.org/10.1021/acs.orglett.3c02548. |
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