Kinetics of 5-exo cyclizations of N-alkyl-4-pentenaminyl radicals and β-fragmentations of β-(dialkylamino)alkyl radicals

Journal of the American Chemical Society

Volumn 119, Issue 20, 1997, Pages 4569-4577

  Newcomb, Martin ^a   Musa, Osama M ^a   Martinez, Felix N ^a   Horner, John H ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL;

ARTICLE; CALCULATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CYCLIZATION; ENERGY; PHOTOLYSIS;

EID: 0030938147     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964318w     Document Type: Article

References (52)

1. (a) Maxwell, B. J.; Tsanaktsidis, J. J. Chem. Soc., Chem. Commun. 1994, 533-534.
2. (b) Maxwell, B. J.; Tsanaktsidis, J. J. Am. Chem. Soc. 1996, 118, 4276-4283.
3. (a) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron Lett. 1991, 32, 6441-6444.
4. (b) Beckwith, A. L. J.; Maxwell, B. J.; Tsanaktsidis, J. Aust. J. Chem. 1991, 44, 1809-1812.
5. (c) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron Lett. 1992, 33, 4993-4994.
6. (d) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron 1994, 50, 1295-1310.
7. (e) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron 1994, 50, 1275-1294.
8. Maxwell, B. J.; Schiesser, C. H.; Smart, B. A.; Tsanaktsidis, J. J. Chem. Soc., Perkin Trans. 2 1994, 2385-2387. Correction: Maxwell, B. J.; Schiesser, C. H.; Smart, B. A.; Tsanaktsidis, J. J. Chem. Soc., Perkin Trans. 2 1995, 1245.
9. Maxwell, B. J.; Schiesser, C. H.; Smart, B. A.; Tsanaktsidis, J. J. Chem. Soc., Perkin Trans. 2 1994, 2385-2387. Correction: Maxwell, B. J.; Schiesser, C. H.; Smart, B. A.; Tsanaktsidis, J. J. Chem. Soc., Perkin Trans. 2 1995, 1245.
10. Newcomb, M.; Deeb, T. M.; Marquardt, D. J. Tetrahedron 1990, 46, 2317-2328.
11. Mackiewicz, P.; Furstoss, R. Tetrahedron 1978, 34, 3241-3260. Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350. Esker, J. L.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: San Diego, 1993; Vol. 58, pp 1-45.
12. Mackiewicz, P.; Furstoss, R. Tetrahedron 1978, 34, 3241-3260. Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350. Esker, J. L.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: San Diego, 1993; Vol. 58, pp 1-45.
13. Mackiewicz, P.; Furstoss, R. Tetrahedron 1978, 34, 3241-3260. Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350. Esker, J. L.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: San Diego, 1993; Vol. 58, pp 1-45.
14. Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862-3868.
15. Newcomb, M.; Marquardt, D. J.; Kumar, M. U. Tetrahedron 1990, 46, 2345-2352.
16. Newcomb, M. Tetrahedron 1993, 49, 1151 -1176.
17. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739-7742.
18. Newcomb, M.; Tanaka, N.; Bouvier, A.; Tronche, C.; Horner, J. H.; Musa, O. M.; Martinez, F. N. J. Am. Chem. Soc. 1996, 118, 8505-8506.
19. The acronym PTOC derives from pyridine-2-thione oxycarbonyl. PTOC esters are actually anhydrides of a carboxylic acid and the thiohydroxamic acid N-hydroxypyridine-2-thione, and PTOC carbamates are anhydrides of a carbamic acid and the thiohydroxamic acid.
20. Barton, D. H. R.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1988, 44, 5479-5486
21. Castagnino, E.; Corsano, S.; Barton, D. H. R. Tetrahedron Lett. 1989, 30, 2983-2986.
22. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick,T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921.
23. Falvey, D. E.; Schuster, G. B. J. Am. Chem. Soc. 1986, 108, 7419-7420. DeCosta, D. P.; Pincock, J. A. J. Am. Chem. Soc. 1989, 111, 8948-8950.
24. Falvey, D. E.; Schuster, G. B. J. Am. Chem. Soc. 1986, 108, 7419-7420. DeCosta, D. P.; Pincock, J. A. J. Am. Chem. Soc. 1989, 111, 8948-8950.
25. Ha, C; Musa, O. M.; Martinez, F. N.; Newcomb, M. J. Org. Chem. 1997, 62, 0000-0000.
26. Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493-6496.
27. Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, 1996.
28. The G2 (Gaussian-2) method was found to give a mean absolute error of only 1.3 kcal/mol for a test set of 125 well-characterized energy differences; see: Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople J. A. J. Phys. Chem. 1990, 94, 7221-7230.
29. 3N computed by these two methods differed by 25, 21, and 17 kcal/mol, respectively.
30. Jursic, B. S. J. Mol. Struct.: THEOCHEM 1996, 366, 103-108.
31. Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 328-331.
32. (a) Michejda, C. J.; Campbell, D. H.; Sieh, D. H.; Koepke, S. R. In Organic Free Radicals; Pryor, W. A., Ed.; American Chemical Society: Washington, DC, 1978; Chapter 18.
33. (b) Newcomb, M.; Burchill, M. T. J. Am. Chem. Soc. 1983, 105, 7759-7760.
34. (c) Newcomb, M.; Park, S.-U.; Kaplan, J.; Marquardt, D. J. Tetrahedron Lett. 1985, 26, 5651-5654.
35. Newcomb, M.; Horner, J. H.; Filipkowski, M. A.; Ha, C.; Park, S. U. J. Am. Chem. Soc. 1995, 117, 3674-3684.
36. Roubaud, V.; Lemoigne, F.; Mercier, A.; Tordo, P. Synth. Commun. 1996, 26, 1507-1516.
37. Crich, D. Private communication.
38. Crich, D.; Jiao, X. Y.; Yao, Q. W.; Harwood, J. S. J. Org. Chem. 1996, 61, 2368-2373. Crich, D.; Yao, Q. W. J. Org. Chem. 1995, 60, 84-88.
39. Crich, D.; Jiao, X. Y.; Yao, Q. W.; Harwood, J. S. J. Org. Chem. 1996, 61, 2368-2373. Crich, D.; Yao, Q. W. J. Org. Chem. 1995, 60, 84-88.
40. Allen, R. P.; Roberts, B. P.; Willis, C. R. J. Chem. Soc., Chem. Commun. 1989, 1387-1388.
41. 3SnH). Under these conditions, one would expect to observe about 10% yield of ring-opened product 5 if the diselenide was not present. In fact, GC analysis indicated the formation of 4 in 90% yield based on the limiting tin hydride, and ring-opened product 5 was not observed at a detection limit of 0.1%.
42. Neumann, W. P. The Organic Chemistry of Tin; Wiley-Inter-science: London, 1970; p 173 and references cited therein.
43. Horner, J. H.; Martinez, F. N.; Musa, O. M.; Newcomb, M.; Shahin, H. E. J. Am. Chem. Soc. 1995, 117, 11124-11133.
44. Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94.
45. Horsma, D. A.; Nash, C. P. J. Phys. Chem. 1968, 72, 2351-2358.
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montogomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, A.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
47. Pople, J. A.; Nesbet, R. K. J. Chem. Phys. 1954, 22, 571-572.
48. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939-947.
49. Hartiharan, P. C.; Pople. J. A. Theor. Chim. Acta 1973, 28, 213-222.
50. Schlegel, H. B. J. Chem. Phys. 1986, 84, 4530-4537.
51. Montgomery, J. A.; Ochterski, J. W.; Peterson, G. A. J. Chem. Phys. 1994, 101, 5900-5909.
52. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.