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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.
Additional recommended knowledge
The treatment of tosylhydrazones with alkyl lithium reagents is called the Shapiro reaction.
The first step of the Bamford-Stevens reaction is the formation of the diazo compound 3.
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.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Bamford-Stevens_reaction". A list of authors is available in Wikipedia.|