Thiyl radical

In chemistry, a thiyl radical has the formula RS, sometimes written RS^• to emphasize that they are free radicals. R is typically an alkyl or aryl substituent. Because S–H bonds are about 20% weaker than C–H bonds, thiyl radicals are relatively easily generated from thiols RSH.[1] Thiyl radicals are intermediates in the thiol-ene reaction, which is the basis of some polymeric coatings and adhesives. They are generated by hydrogen-atom abstraction from thiols using initiators such as AIBN:[2]

RN=NR → 2 R^• + N₂

R^• + R′SH → R′S^• + RH

Thiyl radicals are also invoked as intermediates in some biochemical reactions.

References

Dénès, F.; Pichowicz, M.; Povie, G.; Renaud, P. (2014). "Thiyl Radicals in Organic Synthesis". Chemical Reviews. 114 (5): 2587–2693. doi:10.1021/cr400441m. PMID 24383397.
Hoyle, C. E.; Lee, T. Y.; Roper, T. (2004). "Thiol–enes: Chemistry of the Past with Promise for the Future". Journal of Polymer Science Part A: Polymer Chemistry. 42 (21): 5301–5338. Bibcode:2004JPoSA..42.5301H. doi:10.1002/pola.20366.

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[1] Dénès, F.; Pichowicz, M.; Povie, G.; Renaud, P. (2014). "Thiyl Radicals in Organic Synthesis". Chemical Reviews. 114 (5): 2587–2693. doi:10.1021/cr400441m. PMID 24383397.

[2] Hoyle, C. E.; Lee, T. Y.; Roper, T. (2004). "Thiol–enes: Chemistry of the Past with Promise for the Future". Journal of Polymer Science Part A: Polymer Chemistry. 42 (21): 5301–5338. Bibcode:2004JPoSA..42.5301H. doi:10.1002/pola.20366.