Posted by: Mark Foreman | February 13, 2016

Tin hydride reductions

Dear Reader,

Recently one of my readers asked about triphenyl tin hydride as a reducing agent, this is a reagent which will operate in a very different way to the anionic hydride reagents such as sodium borohydride which I have discussed in another post.

I would not expect triphenyl tin hydride or the more common tributyl tin hydride to be a nucelophile which is able to deliver a hydrogen atom to a carbonyl carbon, instead I would expect these reagents to act as reducing agents in free radical reactions. If we consider an alkyl halide then the following reaction mechanism can occur.

First a tin centred radical such as a tributyl tin radical will react with alkyl halide to form an alkyl radical and a tributyl tin halide. The alkyl radical will then react with the tributyl tin hydride to form an alkyl hydride (alkane) and a tin centred radical. Thus we can have a chain reaction. Now you have the words here is a diagram.

Reduction of a alkyl halide by a tin hydride reagent

Reduction of a alkyl halide by a tin hydride reagent

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