Cesium Carboxylates in Dimethylformamide. Reagents for Introduction of Hydroxyl Groups by Nucleophilic Substitution and for Inversion of Configuration of Secondary Alcohols

Journal of Organic Chemistry

Volumn 46, Issue 21, 1981, Pages 4321-4323

  Kruizinga, Wim H ^a   Strijtveen, Bert ^a   Kellogg, Richard M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000588080     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00334a055     Document Type: Article

References (11)

1. Wang, S. S.; Gisin, B. F.; Winter, D. P.; Makofske, R.; Kulesha, I. D.; Tzougraki, C.; Meienhofer, J. J. Org. Chem. 1977, 42, 1286.
2. Kruizinga, W. H.; Kellogg, R. M. J. Am. Chem. Soc., in press; J. Chem. Soc., Chem. Commun. 1979, 286.
3. Review: Mitsunobu, O. Synthesis 1981,1.
4. Corey, E. J.; Nicolaou, K. C.; Shibasaki, M.; Machida, Y.; Shiner, C. S. Tetrahedron Lett. 1975,3183.
5. See also: Sawyer, D. T.; Gibian, M. J. Tetrahedron 1979, 35,1471.
6. Mitsunobu, O.; Eguchi, M. Bull. Chem. Soc. Jpn. 1971,44, 3427.
7. San Filippo, J., Jr.; Chern, C.-I.; Valentine, J. S. J. Org. Chem. 1975, 40, 1678.
8. Bose, A. K.; Lai, B.; Hoffman, W. A.; Manhas, M. S. Tetrahedron Lett. 1973, 1619.
9. For a recent report on the use of cesium fluoride in DMF as a catalyst see: (a) Mukaiyama, T.; Murakami, M.; Yamaguchi, M. Chem. Lett. 1980,529.
10. Mukaiyama, T.; Pai, F.-C.; Onaka, M.; Narasaka, K. Chem. Lett. 1980, 563.
11. Seebach, D.; Hungerbuhler, E.; Schnurrenberger, P.; Weidmann, B.; Zuger, M., submitted for publication in Synthesis.