New approaches to the Cannizzaro and Tishchenko reactions

Synthetic Communications

Volumn 39, Issue 24, 2009, Pages 4473-4478

  Chandrasekhar, Sosale ^a   Srimannarayana, Malempati ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Benzaldehyde; Cannizzaro; Hydrophobic; Oxidation; Reduction; Tishchenko

Indexed keywords

ALDEHYDE; BENZALDEHYDE; BENZOIC ACID; BENZYL ALCOHOL; BENZYL BENZOATE; HYDROXIDE; METHOXIDE SODIUM; REAGENT; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CANNIZZARO REACTION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HYDROPHOBICITY; OXIDATION REDUCTION REACTION; REACTION TIME; TEMPERATURE; TISHCHENKO REACTION;

EID: 74549222955     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902916049     Document Type: Article

References (7)

1. Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 6th ed.; John Wiley: Hoboken, NJ, 2007; pp. 1863, 1865.
2. Mojtahedi, M. M.; Akbarzadeh, E.; Sharifi, R.; Abaee, M. S. Lithium bromide as a flexible, mild, and recyclable reagent for solvent-free Cannizzaro, Tishchenko, and Meerwein-Ponndorf-Verley reactions. Org. Lett. 2007, 9, 2791-2793.
3. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 4th ed.; Longman: Harlow, 1978; p. 790.
4. Zuyls, A.; Roesky, P. W.; Deacon, G. B.; Konstas, K.; Junk, P. C. Lanthanide formamidinates as improved catalysts for the Tishchenko reaction. Eur. J. Org. Chem. 2008, 693-697.
5. Seki, T.; Nakajo, K.; Onaka, M. The Tishchenko reaction: A classic and practical tool for ester synthesis. Chem. Lett. 2006, 35, 824-829.
6. Gokel, G. W.; Gerdes, H. M.; Rebert, N. W. Crown complex and ammonium ion effects in the Cannizzaro reaction. Tetrahedron Lett. 1976, 17, 653-656.
7. Swain, C. G.; Powell, A. L.; Lynch, T. J.; Alpha, S. R.; Dunlap, R. Reduction of benzaldehyde by methoxide ion in aqueous methanol. J. Am. Chem. Soc. 1979, 101, 3584-3587