A practical decarboxylative hydroxylation of carboxylic acids

Tetrahedron

Volumn 54, Issue 24, 1998, Pages 6751-6756

  Barton, Derek H R ^a   Géro, Stéphane D ^b   Holliday, Pascale ^b   Quiclet Sire, Béatrice ^b   Zard, Samir Z ^b,c  

^a TEXAS A AND M UNIVERSITY   (United States)

^b CNRS   (France)

^c LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER; OXYGEN; THIAZOLE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; DECARBOXYLATION; DECOMPOSITION; HYDROXYLATION; IRRADIATION; PRIORITY JOURNAL; REDUCTION;

EID: 0032508065     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00337-8     Document Type: Article

References (16)

1. 1. The conversion of a carboxylic acid into the nor-alcohol using ionic reactions is usually a multistep procedure. One example, which proceeds via the nor-aldehyde or ketone, is the Barbier-Wieland degradation protocol, used in the early transformation of bile acids into pregnane derivatives: Fieser, L. F.; Fieser, M. Steroids ; Reinhold Publishing Corp.: New York, 1959
2. 2. (a) Fossey, J.; Lefort, D. Tetrahedron 1980, 36, 1022-1036.
3. (b) Lefort, D.; Fossey, J.; Gruselle, M.; Nedelec, J.-Y.; Sorba, J. Tetrahedron 1985, 41, 4237-4252.
4. (c) Denney, D. B.; Sherman, N. J. Org. Chem. 1965, 30, 3760-3761.
5. 3. (a) For reviews of this reaction, see: (a) Barton, D. H. R. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993.
6. (b) Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413-1432.
7. (c) Barton, D. H. R.; Zard, S. Z. Pure & Appl Chem., 1986, 58, 675-684.
8. 4. Barton, D. H. R.; Crich, D.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1984, 242-244; Tetrahedron 1985, 41, 3901-3924.
9. 4. Barton, D. H. R.; Crich, D.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1984, 242-244; Tetrahedron 1985, 41, 3901-3924.
10. 5. (a) Barton, D. H. R.; Bridon, D; Zard, S. Z. J. Chem. Soc. Chem. Commun. 1985, 1066-1067; Tetrahedron 1989, 45, 2615-2626.
11. 5. (a) Barton, D. H. R.; Bridon, D; Zard, S. Z. J. Chem. Soc. Chem. Commun. 1985, 1066-1067; Tetrahedron 1989, 45, 2615-2626.
12. (b) Barton, D. H. R.; Ozbalik, N.; Schmitt, M. Tetrahedron Lett., 1989, 30, 3263-3266.
13. 6 Zhu, J.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1995, 51, 5099-5116.
14. 7. Barton, D. H. R.; Crich, D.; Kretzschmar, G. Tetrahedron Lett. 1984, 25, 1055-1058; J. Chem. Soc. Perkin Trans. 1 1986, 39-53.
15. 7. Barton, D. H. R.; Crich, D.; Kretzschmar, G. Tetrahedron Lett. 1984, 25, 1055-1058; J. Chem. Soc. Perkin Trans. 1 1986, 39-53.
16. 8. Itaya, T.; Iida, T.; Shimizu, S.; Mizutani, A.; Morizue, M.; Sugimoto, Y.; Tachinaka, M. Chem. Pharm. Bull 1993, 41, 252-261.