Excited precursor reactivity, fast 1,2-H shifts, and diffusion- controlled methanol insertion in 1,2-diphenylalkylidenes

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5139-5147

  Motschiedler, Krista ^a   Gudmundsdottir, Anna ^b,c   Toscano, John P ^b,d   Platz, Matthew ^b   Garcia Garibay, Miguel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c UNIVERSITY OF CINCINNATI   (United States)

^d JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ALKYLIDENE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; DIFFUSION; DRUG SYNTHESIS; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033000828     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990172i     Document Type: Article

References (49)

1. Armstrong, B. M.; McKee, M. L.; Shevlin, P. B. J. Am. Chem. Soc. 1995, 117, 3685-3689.
2. Freeman, P. K. J. Am. Chem. Soc. 1998, 120, 1619-1620.
3. Matzinger, S.; Fulscher, M. P. J. Phys. Chem. 1995, 99, 10747-10761.
4. Lim, M. L.; Worthington, S. E.; Dulles, F. J.; Cramer, C. J. In Density Functional Calculations of Radicals and Diradicals; Laird, B. B., Ziegler, T., Ross, R., Eds.; American Chemical Society: Washington, DC, 1996.
5. Cramer, C. J.; Dulles, F.; Falvey, D. E. J. Am. Chem. Soc. 1994, 116, 9787-9788.
6. Carter, E. A.; Goddard, W. A. J. Phys. Chem. 1987, 91, 4651-4652.
7. Irikura, K. K.; Goddard, W. A.; Beauchamp, J. L. J. Am. Chem. Soc. 1992, 114, 48-51.
8. Sulzbach, H. M.; Bolton, E.; Lenoir, D.; Schleyer, P. v. R.; Schaefer, H. F. J. Am. Chem. Soc. 1996, 118, 9908-9914.
9. Mendez, F.; Garcia-Garibay, M. A., manuscript in preparation.
10. Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F.; Hadad, C. M. J. Am. Chem. Soc. 1997, 119, 5682-5689.
11. Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Phys. Chem. 1998, 102, 8467-8476.
12. Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535-1542.
13. Schaefer, H. F.; Ma, B. J. Am. Chem. Soc. 1994, 116, 3539-3542.
14. Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 9148-9156.
15. Keating, A. E.; Shin, S. H.; Houk, K. N.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1997, 119, 1474-1475.
16. Gonzales, C.; Reatrepo-Cossio, A.; Marquez, M.; Wiberg, K. B.; De Rosa, M. J. Phys. Chem. 1998, 102, 2732-2738.
17. Platz, M. S.; White, W. R.; Modarelli, D. A.; Celebi, S. Res. Chem. Intermed. 1994, 20, 175-193.
18. Moss, R. A. Adv. Carbene Chem. 1994, 1, 59-88.
19. Jackson, J. E.; Platz, M. S. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press Inc.: New York, 1994; Vol. 1, pp 89-160.
20. Chang, K. T.; Schechter, H. J. Am. Chem. Soc. 1979, 101, 5082-5083.
21. Yamamoto, Y.; Murahashi, S. I.; Moritani, I. Tetrahedron 1975, 31, 2663-2667.
22. Frey, H. M.; Stevens, I. D. R. J. Chem. Soc. 1965, 1701-1705.
23. Fox, J. M.; Guillen Scacheri, J. E.; Jones, K. G. L.; Jones, M., Jr.; Shelvin, P. B.; Armstrong, B.; Sztyrbicka, R. Tetrahedron Lett. 1992, 33, 5021-5024.
24. Celebi, S.; Leyva, S.; Modarelli, D. A.; Platz, M. S. J. Am. Chem. Soc. 1993, 115, 8613-8620.
25. Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287-294.
26. Garcia-Garibay, M. A. J. Am. Chem. Soc. 1993, 115, 7011-7012.
27. Garcia-Garibay, M. A.; Theroff, C.; Shin, S. H.; Jernelius, J. Tetrahedron Lett. 1993, 52, 8415-8418.
28. Shin, H. S.; Keating, A. E.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1996, 118, 7626-7627.
29. Trozzolo, A. M.; Wasserman, E. In Structure of Arylcarbenes; Moss, R. A., Jones, M. J., Eds.; John Wiley & Sons: New York, 1975; Vol. 2, pp 185-206.
30. Tomioka, H.; Hayashi, N.; Izawa, Y.; Senthilnathan, V. P.; Platz, M. S. J. Am. Chem. Soc. 1983, 105, 5053-5057.
31. Shin, S. H.; Cizmeciyan, D.; Keating, A. E.; Khan, S. I.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1997, 119, 1859-1868.
32. Motschiedler, K. R.; Toscano, J. P.; Garcia-Garibay, M. A. Tetrahedron Lett. 1997, 38, 949-952.
33. Kirmse, W. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press Inc.: New York, 1994; Vol. 1, pp 1-57.
34. Griller, D.; Nazran, A. S.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 198-202.
35. Eisenthal, K. B.; Turro, N. J.; Sitzmann, E. V.; Gould, I. R.; Hefferon, G.; Langan, J.; Cha, Y. Tetrahedron 1985, 41, 1543-1554.
36. Sugiyama, M. H.; Celebi, S.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 966-973.
37. Nickon, A. Acc. Chem. Res. 1993, 26, 84-89.
38. Smith, L. I.; Howard, K. L. Org. Synth. 1955, 3, 351-352.
39. Pomerantz, M.; Witherup, T. H. J. Am. Chem. Soc. 1973, 95, 5977-5988.
40. Griller, D.; Nazran, A. S.; Scaiano, J. C. Tetrahedron 1985, 41, 1525-1530.
41. Kopecky, K. R.; Hammond, G. S.; Leermakers, P. A. J. Am. Chem. Soc. 1981, 83, 1397-1398.
42. Kopecky, K. R.; Hammond, G. S.; Leermakers, P. A. J. Am. Chem. Soc. 1962, 84, 1015-1019.
43. Moritani, I.; Yamamoto, Y.; Murahashi, S.-I. Tetrahedron Lett. 1968, 5697-5701.
44. Jackson, J. E.; Soundararajan, N.; Platz, M. S.; Liu, M. T. H. J. Am. Chem. Soc. 1988, 110, 5595-5596.
45. Soundararajan, N.; Jackson, J. E.; Platz, M. S.; Liu, M. T. H. Tetrahedron Lett. 1988, 29, 3419-3422.
46. Turro, N. J. Modern Molecular Photochemistry; Benjamin/ Cummings Publishing Co.: Menlo Park, 1978.
47. Liu, M. T. H.; Bonneau, R. J. Am. Chem. Soc. 1996, 118, 8098-8101.
48. LaVilla, J. A.; Goodman, J. L. J. Am. Chem. Soc. 1989, 111, 6877-6878.
49. Liu, M. T. H.; Bonneau, R. J. Am. Chem. Soc. 1990, 112, 3915-3919.