Removing functional groups: Radical Substitution of Br by H

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Tributyltin hydride (methyl is used in place of butyl for the animation) can be used to reduce various functional groups including halogens, sulfides and selenides. The reaction proceeds by homolysis of the tin-hydrogen bond either with light or AIBN, followed by abstraction of the funtional group. Radical substitution reactions can also be used to remove functional groups from molecules.