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Barton–Kellogg reaction
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Barton–Kellogg reaction : ウィキペディア英語版
Barton–Kellogg reaction
The Barton–Kellogg reaction is a coupling reaction between a diazo compound and a thioketone through a diazo intermediate forming an alkene.
This reaction was pioneered by Hermann Staudinger, and the reaction also goes by the name Staudinger type diazo-thioketone coupling.
== Reaction mechanism ==
In the reaction mechanism for this reaction the diazo compound is a 1,3-dipole which reacts with the thioketone in a 1,3-dipolar cycloaddition to a thiadiazoline. This intermediate is unstable and through nitrogen gas expulsion and formation of an intermediate thiocarbonyl ylide it forms a stable episulfide. Triphenylphosphine opens the three-membered ring and then forms a sulfaphosphatane in a manner similar to the Wittig reaction. In the final step triphenylphosphine sulfide is expulsed liberating the alkene.

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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