||Chapter 15: Alcohols, Diols
Preparation of Thiols
Reaction type: Nucleophilic substitution
- A convienient source of S
- Reaction of the S system
as a nucleophile with an alkyl halide, R-X, in an SN2
fashion gives an intermediate isothiouronium salt.
- Hydrolysis of the intermediate
provides the thiol, R-SH.
- These steps can be carried out
without isolating the intermediate.
- Overall, this is equivalent to
treating the alkyl halide, R-X, with H2S or HS-
(note: H2S is a toxic gas with a very strong odour).
||© Dr. Ian Hunt, Department of Chemistry, University