Exploring the Photophysical and Photochemical Properties of N -(thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
Photocyclization of N-(thioalkyl)-saccharin was carried out to obtain different polycyclic sultams in good yields. These photoreactions were efficient under inert atmosphere and acetone triplet-sensitized conditions indicating that the triplet excited state is directly involved in the formation of a...
| Autores: | , , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2016 |
| País: | Argentina |
| Recursos: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositório: | CONICET Digital (CONICET) |
| Idioma: | inglês |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/43440 |
| Acesso em linha: | http://hdl.handle.net/11336/43440 |
| Access Level: | Acceso aberto |
| Palavra-chave: | HETEROCYCLE SACCHARIN CYCLIZATION PHOTOINDUCED ELECTRON TRANSFER https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Resumo: | Photocyclization of N-(thioalkyl)-saccharin was carried out to obtain different polycyclic sultams in good yields. These photoreactions were efficient under inert atmosphere and acetone triplet-sensitized conditions indicating that the triplet excited state is directly involved in the formation of annulated products. The presence of molecular oxygen changes product distribution, and only photo-oxygenation products (sulfoxides and sulfones) were found. This result is especially valuable since, by simple changing from nitrogen- to oxygen-saturated solvent conditions, the reaction outcome can be tuned from cyclized to sulfur oxidation products. Additionally, steady-state photolysis, electrochemistry, and laser time-resolved spectroscopic studies confirmed that these reactions mainly proceeded by intramolecular electron transfer (ET) between the triplet excited saccharin moiety and sulfur atom. |
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