Reductive tert-butylation of anils by tert-butylmercury halides

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8988-8991

  Russell, Glen A ^a   Wang, Lijuan ^a   Rajaratnam, Ragine ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000649267     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961544f     Document Type: Article

References (14)

1. Electron Transfer Processes. 61.
2. Russell, G. A.; Yao, C.-F.; Rajaratnam, R.; Kim, B. H. J. Am. Chem. Soc. 1991, 113, 373.
3. Russell, G. A.; Hu, S.; Herron, S.; Baik, W.; Ngoviwatchai, P.; Jiang, W.; Nebgen, M.; Wu, Y.-W. J. Phys. Org. Chem. 1988, 1, 299.
4. Cottrell, T. L. The Strengths of Chemical Bonds; Academic Press: New York, 1954.
5. Alkylmercury(I) species have negligible bond dissociation energies: Gowenlock, B. G.; Polanyi, J. C.; Warehurst, E. Proc. R. Soc. London, Ser. A 1953, 219, 270. The bond dissication energies of HgX' are 23, 16, and 8 mol for X = Cl, Br, and I, respectively: Gaydon, A. G. Dissociation Energies and Spectra of Diatomic Molecules, 3rd ed.; Chapman and Hall: London, 1968.
6. Blaukat, U.; Newmann, W. P. J. Organomet. Chem. 1973, 49, 323.
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8. Qin, L.; Tripathi, G. N. R.; Schuler, R. H. Z. Naturforsch. A 1985, 40, 1026.
9. Russell, G. A.; Ngoviwatchai, P. J. Org. Chem.1989, 45, 1836.
10. If the addition of (-Bu* to 1 is reversible, and if a proton donor increases the rate of conversion of the adduct radical to 2, an apparent increase in substrate reactivity could be observed without substrate protonation. Perhaps the small increase in relative reactivity observed for la in the presence of NH4l reflects this reversibility.
11. Russell, G. A.; Shi, B. Z.; Jiang, W.; Hu, S.; Kim, B. H.; Baik, W. J, Am. Chem. Soc. 1995, 117, 3952.
12. Metgerand, T.; Plank, H. Bull. Soc. Chim. Fr. 1956, 1692.
13. Katritzky, A. R.; Kuzmierkiewicz, W.; Aurrecoechea, J. M. J. Org. Chem. 1987, 52, 844.
14. Reesor, J. W. B.; Wright, G. F. J. Org. Chem. 1957, 22, 375.