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Bamford–Stevens reaction : ウィキペディア英語版
Bamford–Stevens reaction
The Bamford–Stevens reaction is a chemical reaction whereby treatment of tosylhydrazones with strong base gives alkenes. It is named for the British chemist William Randall Bamford and the Scottish chemist Thomas Stevens Stevens (1900–2000). The usage of aprotic solvents gives predominantly Z-alkenes, while protic solvent gives a mixture of E- and Z-alkenes. As an alkene-generating transformation, the Bamford–Stevens reaction has broad utility in synthetic methodology and complex molecule synthesis.
The treatment of tosylhydrazones with alkyl lithium reagents is called the Shapiro reaction.
==Reaction mechanism==
The first step of the Bamford–Stevens reaction is the formation of the diazo compound 3.〔 (''also in the (Collective Volume (1990) 7:438 ) (PDF)'')〕
In protic solvents, the diazo compound 3 decomposes to the carbenium ion 5.
In aprotic solvents, the diazo compound 3 decomposes to the carbene 7.

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