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New selective oxidation of thiols to the corresponding thiolsulfonates with dinitrogen tetroxide: one pot syntheses of thiolsulfonates from thiols

✍ Scribed by Yong H. Kim; Kōichi Shinhama; Daikichi Fukushima; Shigeru Oae

Book ID: 104245582
Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 129 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)94501-0

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✦ Synopsis

We have recently reported that thereactionsof thiols with an equimolar amount of N204 readily afford the thionitrites quantitatively 1) . We have now found that the both aromatic and alkyl thiols reacted readily with excess N204 at low temperatures(ca. -20°C) thiolsulfonates in good yields. RSH 1 RS03H RSS02R 3 eq. N204 ii) t-BuOH 5 3 . Therefore, the corresponding thiolsulfonate, disulfide or sulfonic acid can be prepared selectively by the simple and selective oxidation of the thiol with N204 when the reaction temperature, time and the concentration of N204 were carefully controlled.

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✍ Yong Hae Kirn; Toshikazu Takata; Shigeru Oae 📂 Article 📅 1978 🏛 Elsevier Science 🌐 French ⚖ 248 KB

We have recently reported that oxidations of unsymmetrical thiolsulfinates with peroxy acid 1) or dinitrogen tetraoxide 2) afforded the corresponding symmetrical thiolsulfonates which were undoubtedly derived by the cleavage of sulfur-sulfur bond. We now have found that both aryl-and alkyl unsymmet