Rate Constants for Halogen Atom Transfer from Representative α-halocarbonyl Compounds to Primary Alkyl Radicals

Journal of Organic Chemistry

Volumn 54, Issue 8, 1989, Pages 1826-1831

  Curran, Dennis P ^a   Bosch, Eric ^a   Kaplan, Jere ^b   Newcomb, Martin ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845183485     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00269a016     Document Type: Article

References (13)

1. Recipient of a Sloan Foundation Fellowship, 1985–87. Dreyfus Teacher-Scholar, 1985–89. Eli Lilly Grantee, 1985–87. Merck Faculty Development Awardee, 1986–87. NIH Research Career Development Awardee. 1987–92.
2. Newcomb, M.; Kaplan, J. Tetrahedron Lett. 1987, 28, 1615.
3. Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477. (b) Curran. D. P.: Chang, C. T. J. Org. Chem., in nress.
4. Newcomb, M.; Sanchez, R. M.; Kaplan, J. J. Am. Chem. Soc. 1987, 109, 1195.
5. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
6. Newcomb, M.; Curran, D. P. Acc. Chem. Res. 1988, 21, 206. (b) Newcomb, M.; Kaplan, J.; Curran, D. P. Tetrahedron Lett. 1988, 29, 3451.
7. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979.
8. Barton, D. H. R.; Bridon, D.; Fernandez-Picot, I.; Zard, S. Z. Tetrahedron 1987.,43, 2733.
9. Franz, J. A.; Bushaw, B. A.; Alnajjar, M. S. J. Am. Chem. Soc. 1989, 111, 268; we thank Dr. Franz for communicating this information prior to publication.
10. For a discussion, see: Newcomb, M.; Glenn, A. G. J. Am. Chem. Soc. 1989, 111, 275.
11. Johnson, L. J.; Lusztyk, J.; Wayner, D. D.; Abeywickreyma, A. N.; Beckwith, A. L. J.; Scaiano, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594.
12. Safronenko, E. D.; Afanas’ev, I. B. Zh. Org. Khim. 1968, 4, 2086.
13. Note Added in Proof. Rate constants for iodine atom transfer reactions of the 2-hydroxy-2-methylpropyl radical with ICHoCO2H and ICH2CN at 20 °C in water have been reported to be 1.3 X 107 and 2.0 X 107 M-1 s-1, respectively; cf. Gilbert, B. C.; Norman, R. O. C.; Sealy, R. C. J. Chem. Soc., Perkin Trans. 2 1974, 1435.