Article
Experimental and Theoretical Analysis of the Thiol-Promoted Fragmentation of 2-Halo-3-tosyl-oxanorbornadienes
Author/s | Carranza César, Marina
![]() ![]() ![]() ![]() ![]() Carmona Asenjo, Ana Teresa ![]() ![]() ![]() ![]() ![]() ![]() ![]() Navo, Claudio D. Robina Ramírez, Inmaculada ![]() ![]() ![]() ![]() ![]() ![]() ![]() Fratta, Simone Newburn, Carlos Jimenez-Oses, Gonzalo Moreno Vargas, Antonio José ![]() ![]() ![]() ![]() ![]() ![]() ![]() |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2023 |
Deposit Date | 2023-11-07 |
Published in |
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Abstract | 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. |
Funding agencies | Ministerio de Ciencia e Innovación (MICIN). España Junta de Andalucía European Union (UE) |
Project ID. | PID2020-116460RB-100
![]() PID2021- 125946OB-I00 ![]() CEX2021-001136-S ![]() P20_00532 ![]() 671881 ![]() |
Citation | 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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