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3-Chloroperoxybenzoic acid is a strong oxidizing agent used in the oxidation reactions such as aldehydes and ketones to esters (Bayer-Villiger-Oxidation), olefines to epoxides, sulfides to sulfoxides and sulfones, and amines to nitroalkanes, N-oxides.
Reagent for epoxidation of alkenes: J. Org. Chem., 29, 1976 (1964). Dichloromethane has been recommended as solvent for these reactions, since the peracid is soluble, but the by-product, 3-chlorobenzoic acid, is almost insoluble. For high-yield, stereospecific epoxidation in a two-phase, almost neutral system, see: J. Org. Chem., 44, 1351 (1979). For regioselective epoxidation of the more substituted double bond of a diene, see: Org. Synth. Coll., 5, 467 (1973). For epoxidation in aqueous solution followed by in situ hydrolysis to the trans-diol by 10% sulfuric acid, see: Synth. Commun., 19, 1939 (1989).
Carbonyl compounds undergo the Baeyer-Villiger reaction to give esters or lactones: J. Org. Chem., 29, 2914 (1964). For an extensive review of the Baeyer-Villiger reaction, see: Org. React., 43, 251 (1993).
Primary aliphatic amines are oxidized to nitro-compounds: J. Org. Chem., 31, 524 (1966). Good yields are obtained in 1,2-dichloroethane solution: J. Org. Chem., 44, 659 (1979); 54, 2869 (1989).
Sulfides can be oxidized selectively either to sulfoxides or sulfones: Tetrahedron, 22, 1235 (1966); J. Chem. Soc. (C), 2720 (1969); J. Org. Chem., 35, 2106 (1970).
For the stereospecific oxidation of imines to oxaziridines under phase-transfer conditions, see: Org. Synth. Coll., 8, 546 (1993):
Perfluorooxaziridines have been prepared using acetonitrile as solvent: J. Org. Chem., 58, 4754 (1993).
For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 664 (2007).
WARNING: The reagent has been reported to react exothermically with DMF: Org. Process Res. Dev., 6, 159 (2004).
Ernould, B.; Devos, M.; Bourgeois, J.; Rolland, J.; Vlad, A.; Gohy, J. Grafting of a redox polymer onto carbon nanotubes for high capacity battery materials. J. Mater. Chem. A 2015, 3 (16), 8832-8839.
Giuliano, M. W.; Lin, C.; Romney, D. K.; Miller, S. J.; Anslyn, E. V. A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer-Villiger Oxidation. Ind. Eng. Chem. Res. 2015, 357 (10), 2301-2309.
Hazard Statements: H242-H302-H314-H317-H335
Heating may cause a fire. Harmful if swallowed. Causes severe skin burns and eye damage. May cause an allergic skin reaction. May cause respiratory irritation.
Precautionary Statements: P210-P220-P234-P260-P264b-P270-P271-P272-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P333+P313-P363-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Keep only in original container. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant