- Barbier-Wieland Degradation
-
Barbier-Wieland Degradation
H. Wieland, Ber. 45, 484 (1912); P. Barbier, R. Locquin, Compt. Rend. 156, 1443 (1913).
Stepwise carboxylic acid degradation of aliphatic acids (particularly in sterol side chains) to the next lower homolog. The ester is converted to a tertiary alcohol that is dehydrated with acetic anhydride, and the olefin oxidized with chromic acid to a lower homologous carboxylic acid:
H. Wieland et al., Z. Physiol. Chem. 161, 80 (1926); C. W. Shoppee, Ann. Repts. (Chem. Soc., London) 44, 184 (1947); W. Baker et al., J. Chem. Soc. 1958, 1007; J. R. Dias, R. Ramachandra, Tetrahedron Letters 1976, 3685. Synthetic applications: S. C. Wilcox, J. J. Guadino, J. Am. Chem. Soc. 108, 3102 (1986); C. D. Schteingart, A. E. Hofmann, J. Lipid Res. 29, 1387 (1988). Cf. Krafft Degradation; Miescher Degradation.
Prev: Bart Reaction
Next: Barbier(-type) Reaction - 【Back】【Close 】【Print】【Add to favorite 】
-
Health and Chemical more >
-
Hot Products
- 68411-27-8 Benzoic acid, C12-15-alkyl esters
- 118-58-1 Benzyl salicylate
- 144-68-3 Zeaxanthin
- 20859-73-8 Aluminum phosphide
- 16109-82-3 iodobis(triphenylphosphino)copper
- 106-53-6 4-Bromothiophenol
- 42252-34-6 Carbamic chloride,N-ethyl-N-methyl-
- 84170-73-0 Polyoxy(methyl-1,2-ethanediyl), .alpha.,.alpha.-1,6-hexanediylbis.omega.-(1-oxo-2-propenyl)oxy-
- 133654-02-1 POLYGLYCERYL-3 CAPRATE
- 142-84-7 Dipropylamine
- 7790-21-8 Potassium periodate
- 10097-16-2 Carbamic acid,N,N'-(methylenedi-4,1-phenylene)bis-, C,C'-diethyl ester