Stereochemistry of the Wacker Reaction: Modes of Addition of Hydroxide, Methoxide, and Phenyl at High and Low [Cl-]. A Study Using Chirality Transfer

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7082-7083

  Hamed, Othman ^a   Thompson, Charles ^a,b   Henry, Patrick M ^a  

^a LOYOLA UNIVERSITY CHICAGO   (United States)

^b UNIVERSITY OF MONTANA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000331108     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971051q     Document Type: Article

References (16)

1. For general discussion and references, see: Henry, P. M. Palladium Catalyzed Oxidation of Hydrocarbons; D. Reidel: Dordrecht, Holland, 1980; pp 41-84.
2. Stille, J. K.; James, D. E. J. Organomet. Chem. 1976, 108, 401-408.
3. Stille, J. K.; Divakarumi, R. J. Organomet. Chem. 1979, 169, 239-248.
4. Åkermark, B.; Söderberg, B. C.; Hall, S. S. Organometallics 1987, 6, 2608-2610.
5. Bäckvall, J. E.; Åkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411-2416.
6. Gregor N.; Zaw, K.; Henry, P. M. Organometallics 1984, 3, 1251-1256.
7. Henry, P. M.; Lee, H. B. Can. J. Chem. 1976, 54, 1726-1738.
8. Dumlao, C. M.; Francis, J. W.; Henry, P. M. Organometallics 1991, 10, 1400-1405.
9. See reference 10 for a discussion of chirality transfer.
10. (a) Francis, J. W.; Henry, P. M. Organometallics 1991, 10, 3498-3503.
11. (b) Francis, J. W.; Henry, P. M. Organometallics 1992, 11, 2832-2836.
12. A reviewer pointed out that it is also assumed that the same π-complex is attacked regardless of nucleophile. Certainly methanol and water are so similar that this assumption must be valid. Also there appears to be no reason coordinated hydroxide or methoxide would add to a different π-complex than coordinated phenyl.
13. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5526-5531.
14. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518-5526.
15. (a) Heck, R. F. J. Am. Chem. Soc. 1969, 91, 6707-6714.
16. (b) Henry P. M.; Ward, G. A. Ibid. 1972, 94, 673-674.