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Bamford-Stevens Reaction

Bamford-Stevens Reaction. Jannat Suwan. : Table of Contents. Objectives. Background. Reaction and Mechanism. Application and recent Literature. Conclusion. References. Objectives. Tosylhydrazones give alkenes upon treatment with strong bases.

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Bamford-Stevens Reaction

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  1. Bamford-Stevens Reaction Jannat Suwan

  2. :Table of Contents • Objectives. • Background. • Reaction and Mechanism. • Application and recent Literature. • Conclusion. • References.

  3. Objectives Tosylhydrazones give alkenes upon treatment with strong bases. This reaction may be used to effect the overall transformation of a ketone to an alkene. Intramolecular and intermolecular pathways to nortricyclane in Bamford-Stevens reactions.

  4. Background The Bamford–Stevens reaction is a chemical reaction whereby treatment of tosylhydrazones(p-Toluenesulfonyl hydrazones)with strong base gives alkenes.It is named for the British chemist William Randall Bamford and the Scottish chemist Thomas Stevens (1900–2000). The usage of aprotic solvent gives predominantly Z-alkenes, while protic solvent gives a mixture of E- and Z-alkenes. This reaction may be used to effect the overall transformation of a ketone to an alkene. The treatment of tosylhydrazones with alkyl lithium reagents is called the Shapiro reaction.

  5. Reaction and Mechanism • Mechanism:

  6. In protic solvents: In aprotic solvents: The desired alkene is obtained in high yield in aprotic solvents.

  7. Application and recent Literature This reaction has wide applications in the preparation of alkenes. The highly substituted alkenes, and depending on the reaction conditions (e.g., bases used, solvents), other types of products rather than alkenes can also be prepared.

  8. Conclusion This reaction is the transformation of ketones and aldehydes into alkenes and is known as the Bamford–Stevens reaction. This reaction is also referred to as the Bamford–Stevens olefination. Strong bases have been used in this reaction.

  9. References en.wikipedia.org/wiki/Bamford–Stevens_reaction www.adichemistry.com/.../namedreactions/bamfordstevens/bamford-stevens- 1.html onlinelibrary.wiley.com/doi/10.1002/9780470638859.conrr046/pdf www.organic-chemistry.org › ... › Name Reactions. pubs.acs.org/doi/abs/10.1021/ja00775a035

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