Natural Science Forum / Chemistry / Organic Synthesis / June 2005

NaH or KH + PhSH, generated in situ in reaction mixture.

If NaH or KH happen to be unacceptable for safety reasons or their
mineral oil content (=used as stabilizer), you can perhaps use tBuONa
or tBuOK: the produced t-butanol is fairly innocuous

Using NaH would be a good choice, unfortunately it never
reacts completely even if an excess of PhSH is used.
Any ideas about separating unreacted NaH from PhSNa
on water free conditions?

If you have the anhydrous thiophenol, simply dissolve it a suitable
solvent (THF or an alcohol) and add a stoichiometric amount of the
alkali metal.  I don't recommend adding potassium to a reactive
alcohol, though (boom!).