SN2 reaction of hydrosulfide ion with alkyl halides to give thiols

by James

Description: Alkyl halides (or tosylates) will react with the hydrosulfide ion (HS–) to give thiols.
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{ 3 comments… read them below or add one }

Sachin Thakur. October 17, 2012 at 7:47 am

The explanations given here are point perfect and there is no need for other references.

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Pablo Guerrero September 25, 2014 at 11:12 pm

Don’t you have to use DMSO as the solvent for the second example?

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James September 26, 2014 at 1:15 pm

A polar aprotic solvent like DMSO or acetonitrile would certainly be helpful for these reactions. It’s unlikely to have any competition with the E2 since the sulfide anion is not particularly basic (good threshold is the E2 doesn’t compete if the pKa of the conjugate acid is 12 or below. Thiols have a pKa of 12).

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