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Barton–McCombie deoxygenation
The Barton–McCombie deoxygenation is an organic reaction in which an hydroxy functional group in an organic compound is replaced by a hydrogen to give an alkyl group.
It is named for the British chemists Sir Derek Harold Richard Barton (1918–1998) and Stuart W. McCombie.
This deoxygenation reaction is a radical substitution. In the related Barton decarboxylation the reactant is a carboxylic acid.
== Mechanism ==
The reaction mechanism consists of a catalytic radical initiation step and a propagation step. The alcohol (1) is first converted into a xanthate (2). Then, tributylstannane 3 is decomposed by AIBN 8 into a tributylstannyl radical 4. The tributyltin radical abstracts the xanthate group from 2 leaving an alkyl radical 5 and tributyltin xanthate (7). The sulfur tin bond in this compound is very stable and provides the driving force for this reaction. The alkyl radical in turn abstracts a hydrogen atom from a new molecule of tributylstannane generating the desired deoxygenated product (6) and a new radical species ready for propagation.
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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