Permaleic acid: Baeyer-villiger oxidation of cyclododecanone

Journal of Chemical Education

Volumn 90, Issue 8, 2013, Pages 1103-1104

  Taber, Douglass F ^a   Qiu, Jack ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

Hands On Learning Manipulatives; IR Spectroscopy; Laboratory Instruction; Mechanisms of Reactions; Organic Chemistry; Oxidation Reduction; Second Year Undergraduate; Synthesis; Thin Layer Chromatography

Indexed keywords

EID: 84882266230     PISSN: 00219584     EISSN: 19381328     Source Type: Journal    
DOI: 10.1021/ed400083m     Document Type: Article

References (10)

1. Taber, D. F.; Straney, P. J. The Synthesis of Laurolactam from Cyclododecanone via a Beckmann Rearrangement J. Chem. Educ. 2010, 87, 1392
2. Kjonaas, R. A.; Clemons, A. E. The Baeyer-Villiger Oxidation with Trifluoroacetic Acid and Household Sodium Percarbonate J. Chem. Educ. 2008, 85, 827-828
3. Esteb, J. J.; Hohman, J. N.; Schlamadinger, D. E.; Wilson, A. M. A Solvent-Free Baeyer-Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone J. Chem. Educ. 2005, 82, 1837-1838
4. Slawson, C.; Stewart, J.; Potter, R. Biocatalytic Lactone Generation in Genetically Engineered Escherichia coli and Identification of Products by Gas Chromatography-Mass Spectroscopy J. Chem. Educ. 2001, 78, 1533-1534
5. Anoune, N.; Hannachi, H.; Lantéri, P.; Longeray, R.; Arnaud, C. Use of Theoretical Chemistry To Explain Baeyer-Villiger Oxidations of Methoxy Aromatic Aldehydes J. Chem. Educ. 1998, 75, 1290-1290
6. Stephan, E. Baeyer-Villiger Oxidation of Indan-1-ones: Monitoring of the Reaction by VPC and IR Spectroscopy J. Chem. Educ. 1995, 72, 1142-1143
7. 2, see: Kamae, K.; Obora, Y.; Ishii, Y. Baeyer-Villiger oxidation of cycloalkanones with in situ generated hydrogen peroxide from alcohols and molecular oxygen using NHPI as a key catalyst Bull. Chem. Soc. Jpn. 2009, 82, 891-895
8. For the Baeyer-Villiger oxidation of cyclododecanone with MCPBA (ten days), see: van der Mee, L.; Helmich, F.; de Bruijn, R.; Vekemans, J. A. J. M.; Palmans, A. R. A.; Meijer, E. W. Investigation of Lipase-Catalyzed Ring-Opening Polymerizations of Lactones with Various Ring Sizes: Kinetic Evaluation Macromolecules 2006, 39, 5021-5027
9. 12-acyclic compounds from cyclododecanone J. Chem. Soc., Perkin Trans. 1 1983, 1369-1372
10. Uyama, H.; Takeya, K.; Hoshi, N.; Kobayashi, S. Lipase-Catalyzed Ring-Opening Polymerization of 12-Dodecanolide Macromolecules 1995, 28, 7046-7050