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EspañolBAMFORD-STEVENS REACTION
The 'Bamford-Stevens reaction' is a chemical reaction whereby treatment of tosylhydrazones with strong base gives alkenes.[1][2][3] 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.
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'.[4]
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'.
1.
2. Organic Reactions, , R. H., Shapiro, , , ISBN 0-471-19624-X
3.
4. Tosylhydrazone salt pyrolises: phenyldiazomethanes, , X., Creary, Organic Syntheses, (''also in the Collective Volume (1990) '7':438 (PDF)'')
★ Shapiro reaction
The Bamford-Stevens reaction
The treatment of tosylhydrazones with alkyl lithium reagents is called the Shapiro reaction.
| Contents |
| Reaction mechanism |
| References |
| See also |
Reaction mechanism
The first step of the Bamford-Stevens reaction is the formation of the diazo compound '3'.[4]
The mechanism of the Bamford-Stevens reaction
In protic solvents, the diazo compound '3' decomposes to the carbenium ion '5'.
The mechanism of the Bamford-Stevens reaction
In aprotic solvents, the diazo compound '3' decomposes to the carbene '7'.
The mechanism of the Bamford-Stevens reaction
References
1.
2. Organic Reactions, , R. H., Shapiro, , , ISBN 0-471-19624-X
3.
4. Tosylhydrazone salt pyrolises: phenyldiazomethanes, , X., Creary, Organic Syntheses, (''also in the Collective Volume (1990) '7':438 (PDF)'')
See also
★ Shapiro reaction
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