Ligand coupling mechanism of nucleophilic vinylic substitution of iodonium salts with hypervalent 10-I-3 and 12-I-4 intermediates

Chemistry Letters

Volumn , Issue 9, 1997, Pages 955-956

  Okuyama, Tadashi ^a   Takino, Tomoki ^b   Sato, Koichi ^b   Ochiai, Masahito ^b  

^a OSAKA UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031323821     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.955     Document Type: Article

References (14)

1. M. Ochiai, K. Oshima, and Y. Masaki, J. Am. Chem. Soc., 113, 7059 (1991).
2. M. Ochiai, K. Oshima, and Y. Masaki, Chem. Lett., 1994, 871.
3. 2 The UV spectra were recorded on a spectrometer Shimadzu UV-2200.
4. Details of the reactions of 1a will be presented elsewhere.
5. 6
6. R. L. Amey and J. C. Martin, J. Org. Chem., 44, 1779 (1979). D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 104, 902 (1982).
7. R. L. Amey and J. C. Martin, J. Org. Chem., 44, 1779 (1979). D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 104, 902 (1982).
8. Simulations were carried out using SigmaPlot (Jandel Scientific, San Rafael, CA) by the Marquardt-Levenberg Algorithm.
9. J. Moc. A. E. Dorigo, and K. Morokuma, Chem. Phys. Lett., 204, 65 (1993).
10. For a review, see S. Oae and Y. Uchida, Acc. Chem. Res., 24, 202 (1991).
11. Z. Rappoport, Recl. Trav. Chim. Pays-Bas, 104, 309 (1985). Acc. Chem. Res., 25, 474 (1992).
12. Z. Rappoport, Recl. Trav. Chim. Pays-Bas, 104, 309 (1985). Acc. Chem. Res., 25, 474 (1992).
13. N. P. Hacker, D. V. Leff, and J. L. Dektar, J. Org. Chem., 56, 2280 (1991).
14. With a normal base like carboxylate and amine, 1a undergoes bimolecular a elimination to give the same product 4.