Recommended
More Related Content
What's hot
What's hot (20)
Similar to Baeyer-Villiger Oxidation Mechanism and Applications
Similar to Baeyer-Villiger Oxidation Mechanism and Applications (20)
Recently uploaded
Recently uploaded (20)
Baeyer-Villiger Oxidation Mechanism and Applications
- 1. © Ramaiah University of Applied Sciences 1 Faculty of Pharmacy © Ramaiah University of Applied Sciences 1 Faculty of Pharmacy © Ramaiah University of Applied Sciences 1 Faculty of Pharmacy © Ramaiah University of Applied Sciences 1 Faculty of Pharmacy Baeyer – Villiger Oxidation By Burhanuddin Madriwala M.Pharm – SEM I Department of Pharmaceutical Chemistry M.S Ramaiah University of Applied Sciences
- 2. © Ramaiah University of Applied Sciences 2 Faculty of Pharmacy © Ramaiah University of Applied Sciences 2 Faculty of Pharmacy © Ramaiah University of Applied Sciences 2 Faculty of Pharmacy © Ramaiah University of Applied Sciences 2 Faculty of Pharmacy Contents • Introduction • General reaction • Peroxyacids & Peroxides • Mechanism of reaction • Migration of groups in unsymmetrical ketones • Applications of reaction • Summary • references
- 3. © Ramaiah University of Applied Sciences 3 Faculty of Pharmacy © Ramaiah University of Applied Sciences 3 Faculty of Pharmacy © Ramaiah University of Applied Sciences 3 Faculty of Pharmacy © Ramaiah University of Applied Sciences 3 Faculty of Pharmacy Introduction • First reported by Adolf Von Baeyer & Victor Villiger in 1899. • Used for producing esters from ketones by oxidation. • It involves addition of oxygen atom to carbonyl group of ketone by peroxy compounds in presence of acid or base catalyst. • Principle involved is oxidation & rearrangement i.e. migration of alkyl group. • Peroxy compounds/peroxides are used as the oxidising agents. • Aliphatic & aromatic esters both are produced from acyclic ketones. • Lactones are produced from cyclic ketones.
- 4. © Ramaiah University of Applied Sciences 4 Faculty of Pharmacy © Ramaiah University of Applied Sciences 4 Faculty of Pharmacy © Ramaiah University of Applied Sciences 4 Faculty of Pharmacy © Ramaiah University of Applied Sciences 4 Faculty of Pharmacy General reaction
- 5. © Ramaiah University of Applied Sciences 5 Faculty of Pharmacy © Ramaiah University of Applied Sciences 5 Faculty of Pharmacy © Ramaiah University of Applied Sciences 5 Faculty of Pharmacy © Ramaiah University of Applied Sciences 5 Faculty of Pharmacy Peroxyacids & Peroxides
- 6. © Ramaiah University of Applied Sciences 6 Faculty of Pharmacy © Ramaiah University of Applied Sciences 6 Faculty of Pharmacy © Ramaiah University of Applied Sciences 6 Faculty of Pharmacy © Ramaiah University of Applied Sciences 6 Faculty of Pharmacy Mechanism of reaction
- 7. © Ramaiah University of Applied Sciences 7 Faculty of Pharmacy © Ramaiah University of Applied Sciences 7 Faculty of Pharmacy © Ramaiah University of Applied Sciences 7 Faculty of Pharmacy © Ramaiah University of Applied Sciences 7 Faculty of Pharmacy Migration of R- group: rate determining step • Migration of R – group from the carbon to the oxygen atom & formation of carbocation is the rate determining step. • Migratory aptitude of R- group affects its migration & hence the structure of resulting ester. • R- group can be an alkyl or aryl or their substituted derivatives. Example: isopropyl, tert-butyl, phenyl, o/p- substituted aryl groups etc. • In case of symmetrical ketones, both the R- groups are same. Thus, it does not affect the structure of ester formed. • But when unsymmetrical ketones are involved, the more substituted/electron rich larger group migrates. • Thus the positive charge is delocalised more & so the rearrangement is faster.
- 8. © Ramaiah University of Applied Sciences 8 Faculty of Pharmacy © Ramaiah University of Applied Sciences 8 Faculty of Pharmacy © Ramaiah University of Applied Sciences 8 Faculty of Pharmacy © Ramaiah University of Applied Sciences 8 Faculty of Pharmacy Applications • Formation of lactones
- 9. © Ramaiah University of Applied Sciences 9 Faculty of Pharmacy © Ramaiah University of Applied Sciences 9 Faculty of Pharmacy © Ramaiah University of Applied Sciences 9 Faculty of Pharmacy © Ramaiah University of Applied Sciences 9 Faculty of Pharmacy • Formation of aliphatic & aromatic esters
- 10. © Ramaiah University of Applied Sciences 10 Faculty of Pharmacy © Ramaiah University of Applied Sciences 10 Faculty of Pharmacy © Ramaiah University of Applied Sciences 10 Faculty of Pharmacy © Ramaiah University of Applied Sciences 10 Faculty of Pharmacy Summary • Baeyer Villiger Oxidation was first proposed by Adolf Von Baeyer & Victor Villiger in 1899. • It involves acid – catalysed oxidation of ketones to esters in presence of peroxyacids or peroxides. • Migration of R- group is rate determining step. • It has wide applications in formation of lactones from cyclic ketones, aliphatic & aromatic esters.
- 11. © Ramaiah University of Applied Sciences 11 Faculty of Pharmacy © Ramaiah University of Applied Sciences 11 Faculty of Pharmacy © Ramaiah University of Applied Sciences 11 Faculty of Pharmacy © Ramaiah University of Applied Sciences 11 Faculty of Pharmacy References • Carey, F. and Sundberg, R., 2002. Advanced organic chemistry. 4th ed. New York, Kluwer Academic, pp.798-802. • Mundy, B., Ellerd, M. and Favaloro, F., 2007. Name reactions and reagents in organic synthesis. 2nd ed. Hoboken: Wiley-Interscience, a John Wiley & Sons, pp.48-49.