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Markó–Lam deoxygenation
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Markó–Lam deoxygenation : ウィキペディア英語版
Markó–Lam deoxygenation
The Markó–Lam deoxygenation is an organic chemistry reaction where the hydroxy functional group in an organic compound is replaced by a hydrogen atom to give an alkyl group.〔(【引用サイトリンク】title=Alkane synthesis by deoxygenation )〕〔(マルコ・ラム脱酸素化 Marko-Lam Deoxygenation – ODOOS -合成反応データベース- by Chem-Station ). Chem-station.com (2010-06-06). Retrieved on 2014-01-28.〕 The Markó-Lam reaction is a variant of the Bouveault–Blanc reduction and an alternative to the classical Barton–McCombie deoxygenation. It is named for the Belgian chemists Istvan Marko and Kevin Lam.〔(Kevin Lam ). Sst.nu.edu.kz. Retrieved on 2014-01-28.〕
The main features of the reaction are:
*short reaction time (5 seconds to 5 minutes).
*the use of a stable toluate derivative.
*the use of SmI2/HMPA system or electrolysis instead of the classical and difficult to remove tributyltin hydride.
== Mechanism ==

A hydroxyl group is first derivitised into a stable and very often crystalline toluate derivative. The aromatic ester is submitted to a monoelectronical reduction, by the use of SmI2/HMPA or by electrolysis, to yield the a radical-anion which decomposes into the corresponding carboxylate and into the radical of the alkyl part.
This radical could be used for further chemical reactions or can abstract an hydrogen atom to form the deoxygenated product.

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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