Computational study on nature of transition structure for oxygen transfer from dioxirane and carbonyloxide

Journal of Computational Chemistry

Volumn 19, Issue 12, 1998, Pages 1353-1369

  Baboul, Anwar G ^a   Schlegel, H Bernhard ^a   Glukhovtsev, Mikhail N ^b   Bach, Robert D ^b  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

Ab initio; Carbonyl oxides; Density functional theory; Dioxiranes; Oxidation reactions

Indexed keywords

EID: 0001124459     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(199809)19:12<1353::AID-JCC4>3.0.CO;2-H     Document Type: Article

References (50)

1. (a) F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry Part A (3rd Ed.), Plenum Press, New York, 1990, p. 284;
2. (b) T. H. Lowry and K. S. Richardson, Mechanism and Theory in Organic Chemistry (3rd Ed.), Harper & Row, New York, 1987, p. 367.
3. For reviews, see: (a) R. W. Murray, Chem. Rev., 89, 1187 (1989); (b) W. Adam, L. P. Hadjiarapoglou, R. Curci, and R. Mello, In Organic Peroxides, W. Ando, Ed., Wiley, New York, 1992, p. 195; (c) R. Curci, In Advances in Oxygenated Processes, Vol. 2, A. L. Baumstark, Ed., JAI Press, Greenwich, CT, 1990, p. 1; (d) W. Adam, R. Curci, and J. O. Edwards, Acc. Chem. Res., 22, 205 (1989).
4. For reviews, see: (a) R. W. Murray, Chem. Rev., 89, 1187 (1989); (b) W. Adam, L. P. Hadjiarapoglou, R. Curci, and R. Mello, In Organic Peroxides, W. Ando, Ed., Wiley, New York, 1992, p. 195; (c) R. Curci, In Advances in Oxygenated Processes, Vol. 2, A. L. Baumstark, Ed., JAI Press, Greenwich, CT, 1990, p. 1; (d) W. Adam, R. Curci, and J. O. Edwards, Acc. Chem. Res., 22, 205 (1989).
5. For reviews, see: (a) R. W. Murray, Chem. Rev., 89, 1187 (1989); (b) W. Adam, L. P. Hadjiarapoglou, R. Curci, and R. Mello, In Organic Peroxides, W. Ando, Ed., Wiley, New York, 1992, p. 195; (c) R. Curci, In Advances in Oxygenated Processes, Vol. 2, A. L. Baumstark, Ed., JAI Press, Greenwich, CT, 1990, p. 1; (d) W. Adam, R. Curci, and J. O. Edwards, Acc. Chem. Res., 22, 205 (1989).
6. For reviews, see: (a) R. W. Murray, Chem. Rev., 89, 1187 (1989); (b) W. Adam, L. P. Hadjiarapoglou, R. Curci, and R. Mello, In Organic Peroxides, W. Ando, Ed., Wiley, New York, 1992, p. 195; (c) R. Curci, In Advances in Oxygenated Processes, Vol. 2, A. L. Baumstark, Ed., JAI Press, Greenwich, CT, 1990, p. 1; (d) W. Adam, R. Curci, and J. O. Edwards, Acc. Chem. Res., 22, 205 (1989).
7. (a) R. D. Bach, J. E. Winter, and W. McDouall, J. Am. Chem. Soc., 117, 8586 (1995);
8. (b) R. D. Bach, J. L. Andres, A. L. Owensbey, H. B. Schlegel, and J. J. W. McDouall, J. Am. Chem. Soc., 114, 7207 (1992);
9. (c) R. D. Bach, P. Y. Ayala, and H. B. Schlegel, J. Am. Chem. Soc., 118, 12758 (1996);
10. (d) R. D. Bach, M. N. Glukhovtsev, C. Gonzalez, M. Marquez, C. M. Estevez, A. G. Baboul, and H. B. Schlegel, J. Phys. Chem. A, 101, 6092 (1997);
11. (e) R. D. Bach, M. N. Glukhovtsev, and C. Canepa, J. Am. Chem. Soc., 120, 775 (1998).
12. (a) R. Curci, M. Fiorentino, L. Troisi, J. O. Edwards, and R. H. Pater, J. Org. Chem., 45, 4758 (1980);
13. (b) W. Adam, R. Curci, and J. O. Edwards, Acc. Chem. Res., 22, 205 (1989);
14. W. Adam, R. Curci, L. D'Accolti, A. Dinoi, C. Fusco, F. Gasparrini, R. Kluge, R. Paredes, M. Schulz, A. K. Smerz, L. A. Veloza, S. Weinkötz, and R. Winde, Chem. Eur. J., 3, 105 (1997);
15. (d) W. Adam, R. Paredes, A. K. Smerz, and L. A. Veloza, Liebigs Ann., 547 (1997).
16. (a) R. Criegee and G. Weiner, Liebigs Ann Chem., 9, 546 (1949);
17. (b) F. J. Lovas and R. D. Suenram, Chem. Phys. Lett., 51, 453 (1977);
18. (c) R. D. Suenram and F. J. Lovas, J. Am. Chem. Soc., 100, 5117 (1978).
19. (a) T-K. Ha, H. Kühne, S. Vaccani, and H. H. Günthard, Chem. Phys. Lett., 24, 172 (1974);
20. (b) W. R. Wadt and W. A. Goddard III, J. Am. Chem. Soc., 97, 3004 (1975);
21. (c) L. B. Harding and W. A. Goddard III, J. Am. Chem. Soc., 100, 7180 (1978);
22. (d) G. Karlström, S. Engström, and B. Jönsson, Chem. Phys. Lett., 67, 343 (1979);
23. (e) M. Cantos, M. Merchan, F. Tomas-Vert, and B. O. Roos, Chem. Phys. Lett., 229, 181 (1994).
24. R. Curci, M. Fiorentino, L. Tvoisa, J. O. Edwards, and R. H. Pater, J. Org. Chem., 45, 4758 (1980).
25. (a) R. Mello, M. Fiorentino, O. Sciacovelli, and R. Curci, J. Org. Chem., 53, 3890 (1988);
26. (b) W. Adam, Y-Y. Chan, D. Cremer, J. Gauss, D. Scheutzow, and M. Schindler, J. Org. Chem., 52, 2800 (1987).
27. R. Curci, A. Dinoi, and M. F. Rubino, Pure Appl. Chem., 67, 811 (1995).
28. A. Kirschfeld, S. Muthusamy, and W. Sander, Angew. Chem. Int. Ed. Engl., 33, 2212 (1994).
29. (a) M. Rahman, M. L. McKee, P. B. Shevlin, and R. Sztyrbicka, J. Am. Chem. Soc., 110, 4002 (1988);
30. (b) B. Casper, D. Christen, H-G. Mack, H. Oberhammer, G. A. Argjello, B. Jülicher, M. Kronberg, and H. Willner, J. Phys. Chem., 100, 3983 (1996).
31. (a) W. H. Bunnelle, Chem. Rev., 91, 335 (1991), and references cited therein;
32. (b) D. Cremer, J. Gauss, E. Kraka, J. F. Stanton, and R. J. Bartlett, Chem. Phys. Lett., 209, 547 (1993);
33. (c) E. Kraka, Z. Konkoli, D. Cremer, J. Fowler, and H. F. Schaefer III, J. Am. Chem. Soc., 118, 10595 (1996).
34. (a) W. Adam, W. Haas, and F. Sieker, J. Am. Chem. Soc., 106, 5020 (1984);
35. (b) W. Adam, W. Haas, and B. B. Lohray, J. Am. Chem. Soc., 113, 6202 (1991);
36. (c) W. Adam and D. Golash, Chem. Berl., 127, 1111 (1994).
37. J. J. W. McDouall, J. Org. Chem., 57, 2861 (1992).
38. (a) M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, G. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian-94, Gaussian, Inc., Pittsburgh, PA, 1995;
39. (b) H. B. Schlegel, J. Comput. Chem., 3, 214 (1982).
40. (a) S. Miertus, E. Scrocco, and J. Tomasi, Chem. Phys., 55, 117 (1981);
41. (b) S. Miertus and J. Tomasi, Chem. Phys., 65, 239 (1982);
42. (c) M. A. Aguilar and F. J. O. Olivares del Valle, Chem. Phys., 129, 439 (1989) (N 1.80; P 2.28; S 2.22; C 1.96; O 1.68; H 1.44 Å).
43. D. Cremer, J. Am. Chem. Soc., 101, 7199 (1979).
44. W. Chen and H. B. Schlegel, J. Chem. Phys., 101, 5957 (1994).
45. (a) M. A. P. Dankleff, C. Ruggero, J. O. Edwards, and H. Y. Pyun, J. Am. Chem. Soc., 90, 3209 (1968);
46. (b) R. Curci, R. A. DiPrete, J. O. Edwards, and G. Modena, J. Org. Chem., 35, 740 (1970).
47. 2 as Oxidants, Catalysis by Metal Complexes Series, G. Strukul, Ed., Reidel-Kluwer, Dordrecht, 1992; chapter 3;
48. (b) F. DiFuria and G. Modena, Pure Appl. Chem., 54, 1853 (1982).
49. M. N. Glukhovtsev, R. D. Bach, A. Pross, and L. Radom, Chem. Phys. Lett., 260, 558 (1996).
50. See, for example, V. G. Dryuk, Russian Chem. Rev., 54, 986 (1985), and references therein.