Baeyer Villiger oxidation-Naming reaction.pptx

This is an oxidation reaction where ester products are formed from an aliphatic ketone.
This reaction also occurs in cyclic ketones to form lactones.

1. BAEYER-VILLIGER OXIDATION NILANJANA THAKURIA M PHARM 1 ST SEMESTER DEPT . OF PHARMACEUTICAL CHEMISTRY

2. OVERVIEW INTRODUCTION APPLICATIONS PERACIDS LIMITATIONS REACTION MECHANISM RECENT ADVANCEMENT

3. INTRODUCTION The Baeyer- Villiger Oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts ketones to esters and cyclic ketones to lactones It was discovered by Adolf Baeyer and Victor Villiger in 1899.

4. INTRODUCTION TO PERACIDS A peracid (or peroxyacid) is an acid that contains an additional oxygen atom compared to a regular acid. General formula for peracid is RCOOOH Peracids are powerful oxidizers due to the presence of the peroxy group (-OOH), which is highly reactive. Some of the common peracid are: m- Chloroperbenzoic acid (m-CPBA) Peracetic acid Trifluoroperacetic acid

5. Step 2 : Nucleophilic attack of percarboxylate on the protonatedd ketone REACTION MECHANISM Step 1 : Protonation of the carbonyl group to from a reactive nucleophile and percaboxylate

6. Step 3 : Rearrangement of alkyl group from C-C electron to form a new C-O bond to produce a protonated ester Step 4 : Abstraction of Hydrogen from protonated ester to yield an ester compound REACTION MECHANISM

7. APPLICATIONS ORGANIC SYNTHESIS Synthesis of Lactones : Used to produce important lactones like ε-caprolactone, which is used in polymer synthesis. Pharmaceuticals : The reaction helps in synthesizing intermediates for drug molecules. Natural Products : Used in the modification of steroids and terpenes

8. APPLICATIONS INDUSTRIAL APPLICATIONS Polymer Industry : it is used for the production of biodegradable plastics and fibers. Perfume Industry : used for the synthesis of esters used as fragrance molecules. Agrochemicals : In the production of insecticides and herbicides.

9. Limited Substrate Scope Reagent Sensitivity Overoxidation and By-products Enzyme Inhibition in Biocatalysis LIMITATION

10. Biocatalytic approaches have been optimized by employing engineered cyanobacteria, specifically Synechocystis sp. PCC6803 , to drive photosynthesis-based BVO. The total synthesis of psammaplysins , marine alkaloids with potential antiviral and anticancer properties, was achieved using Baeyer- Villiger oxidation Hydrogen peroxide, a cleaner oxidant, in combination with various catalyst produces only water as a by-product in Bayer Villiger Oxidation making it an environmentally friendly alternative. RECENT ADVANCEMENT

11. REFFERENCE Clayden Jonathan, Greeves Nick, W arren Stuart ‘Organic Chemistry’, 2 nd edition , Oxford University press Röllig , R., Paul, C.E., Rousselot-Pailley , P., Kara, S. and Alphand , V., 2023. Hybrid catalysis for enantioselective Baeyer– Villiger oxidation and stereoselective epoxidation: a Cp* Ir complex to fuel FMN and FAD reduction for flavoprotein monooxygenase modules.  Reaction Chemistry & Engineering ,  8 (12), pp.3117-3123. Fatima, S., Zahoor, A.F., Khan, S.G., Naqvi, S.A.R., Hussain, S.M., Nazeer, U., Mansha, A., Ahmad, H., Chaudhry, A.R. and Irfan, A., 2024. Baeyer– Villiger oxidation: a promising tool for the synthesis of natural products: a review.  RSC advances ,  14 (32), pp.23423-23458.

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