Exploring the Photophysical and Photochemical Properties of N-(Thioalkyl)-saccharins as an Alternative Route to the Synthesis of Tricyclic Sultams
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- 作者：Willber D. Castro-Godoy ; Gabriela Oksdath-MansillaJuan E. Argüello ; Alicia B. Peñéñory
- 刊名：Journal of Organic Chemistry
- 出版年：2017
- 出版时间：January 6, 2017
- 年：2017
- 卷：82
- 期：1
- 页码：101-108
- 全文大小：506K
- ISSN：1520-6904
文摘
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.