17.1: Information About the Reaction

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Figure \(\PageIndex{1}\): Reaction scheme of the formation of sulfide from thiols

Development of the Reaction

Thiols were first discovered in the 19th century. In 1888, de Rey-Pailhade discovered the existence of biothiols when he found out that, when crushed by elemental sulfur, yeast cells contained something that contributes to the formation of hydrogen sulfide.¹

One modification to this reaction is using other organic compounds like arenes and alkanes instead of using halides as substrates.²

Reaction Utility

A potential interconversion in this reaction is between the thiol, base, the thiolate anion, the cation (sodium, for example), and water. The reaction may try to balance itself out if nothing else is added (to reduce the charges of the particles), but it is unlikely because of how acidic the thiol is (and so the thiolate is a weak base).³

As for protecting groups, it depends on the thiol being used. A simple thiol will not need a protecting group, but if the thiol contains other functional groups, then they may need to be protected in the acid-base reaction (proton transfer). The second step is not much of a problem since it will undergo a S2N reaction and not an elimination reaction.³

References

1. Sen, C. K.; Packer, L. Thiol homeostasis and supplements in physical exercise. The American Journal of Clinical Nutrition 2000, 72 (2).

2. Zhang, R.; Ding, H.; Pu, X.; Qian, Z.; Xiao, Y. Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates. Catalysts 2020, 10 (11), 1339.

3. Master Organic Chemistry LLC. Thiols And Thioethers. https://www.masterorganicchemistry.c...nd-thioethers/ (accessed May 2, 2021).

Contributor

Joshua Thielen