Oxygen transfer reactions. 4. Reaction of high valent oxoruthenium compounds with sulfides

Inorganic Chemistry
Sheng LaiDonald G Lee

Abstract

The oxidation of methoxy substituted benzyl phenyl sulfides can be used to distinguish between oxidants that react by single electron transfer (followed by oxygen rebound) and those which react by direct oxygen atom transfer in a two-electron process. Transfer of a single electron results in the formation of an intermediate radical cation, which can undergo C-S bond cleavage and deprotonation reactions leading to the formation of methoxy substituted benzyl derivatives, methoxy substituted benzaldehydes, and diphenyl disulfide. The oxidation of 4-methoxybenzyl phenyl sulfide and 3,4,5-trimethoxybenzyl phenyl sulfide by oxidants known to participate in single electron transfers (Ce(4+), Mn(3+), and Cr(6+)) results in the formation of the corresponding benzaldehydes, benzyl alcohols, benzyl acetates, and benzyl nitrates in variable yields. However, the only products obtained from the oxidation of the same compounds with RuO(4), RuO(4-), and RuO(4)(2-) are sulfoxides and sulfones. Therefore, it is concluded that the oxidation of sulfides by oxoruthenium compounds likely proceeds by a concerted mechanism.

References

Mar 19, 1999·Journal of Toxicology and Environmental Health. Part B, Critical Reviews·X ShiV Vallyathan
May 18, 2000·The Journal of Organic Chemistry·N XieM Thiruvazhi
Jun 9, 2001·The Journal of Organic Chemistry·T OhtaK Yoshizawa
Feb 19, 2002·Chemical Reviews·Takeshi NaotaShun-Ichi Murahashi

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Citations

Jun 29, 2006·Proceedings of the National Academy of Sciences of the United States of America·My Hang V HuynhModi Wetzler
Dec 9, 2015·The Journal of Organic Chemistry·Lili ZhaoYuanhua Wang
May 1, 2015·Inorganic Chemistry·Arijit Singha HazariGoutam Kumar Lahiri
May 19, 2006·Ultrasonics Sonochemistry·Naresh N MahamuniAniruddha B Pandit

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