Absolute rate constant for the reaction of aryl radicals with tri-n-butyltin hydride1

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 805-809

  Garden, S J ^a,b   Avila, D V ^a,b   Beckwith, A L J ^a,c   Bowry, V W ^a,c   Ingold, K U ^a   Lusztyk, J ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b NRCC ^*

^c AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000955889     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951245a     Document Type: Article

References (38)

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15. 16
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18. 20
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22. This concentration gives an optical density, OD ∼ 0.3 at 308 nm in our 7-mm LFP cell.
23. Paul, H.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1978, 100, 4520-4527.
24. In Scheme I this reaction is written as an addition to form a benzylic radical which is the species presumed to be mainly responsible for the grow-in of the 320 nm absorption. However, the global rate constant measured with this substrate includes all modes of reaction including, for example, addition to the aromatic ring.
25. The potential H-atom donors include MMA, the benzylic methyl group of p-iodotoluene and the cyclohexane solvent.
26. 3SnH(D)]/[MMA] ≥ 0.05, [ArI]/[MMA] ≥ 0.3).
27. Barclay, L. R. C.; Griller, D.; Ingold, K U. J. Am. Chem. Soc. 1974, 96, 3011-3012. Brunton, G.; Griller, D.; Barclay, L. R. C. J. Am. Chem. Soc. 1976, 98, 6803-6811. Brunton, G.; Gray, J. A.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1978, 100, 4197-4200.
28. Barclay, L. R. C.; Griller, D.; Ingold, K U. J. Am. Chem. Soc. 1974, 96, 3011-3012. Brunton, G.; Griller, D.; Barclay, L. R. C. J. Am. Chem. Soc. 1976, 98, 6803-6811. Brunton, G.; Gray, J. A.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1978, 100, 4197-4200.
29. Barclay, L. R. C.; Griller, D.; Ingold, K U. J. Am. Chem. Soc. 1974, 96, 3011-3012. Brunton, G.; Griller, D.; Barclay, L. R. C. J. Am. Chem. Soc. 1976, 98, 6803-6811. Brunton, G.; Gray, J. A.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1978, 100, 4197-4200.
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33. Mertens, R.; von Sonntag, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1262-1264. von Sonntag, C. Private communication.
34. 27
35. MMA calculated from the data in Table 4 via eqs V and VI, viz., 5.0 ± 0.6 and 3.5 ± 0.4, respectively (vide infra).
36. Strong, H. L.; Brownawell, M. L.; San Filippo, J., Jr. J. Am. Chem. Soc. 1983, 107, 6526-6528.
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38. Bordwell, F. G.; Carlson, M. W. J. Am. Chem. Soc. 1970, 92, 3370-3377.