On the origin of substrate directing effects in the epoxidation of allyl alcohols with peroxyformic acid

Journal of the American Chemical Society

Volumn 120, Issue 4, 1998, Pages 680-685

  Bach, Robert D ^a   Estévez, Carlos M ^a,b   Winter, Julia E ^c   Glukhovtsev, Mikhail N ^a  

^a UNIVERSITY OF DELAWARE   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CARBONYL DERIVATIVE; FORMIC ACID; PEROXYFORMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ENERGY COST; ENTHALPY; EPOXIDATION; HYDROGEN BOND; NONHUMAN; SURFACE PROPERTY;

EID: 2642633750     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9717976     Document Type: Article

References (63)

1. (a) Plesnicar, B. In The Chemistry of Peroxides; Patai, S., Ed.; John Wiley and Sons: New York, 1983; p 521.
2. (b) Finn, M. G.; Sharpless, K. B. Asymmetric Synth. 1986, 5, 247.
3. (c) Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1971; Vol. II, Chapter 5.
4. For an excellent review on substrate-directable chemical reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. (Washington, D.C.) 1993, 93, 1307.
5. (a) Henbest, H. B.; Wilson, R. A. L. J. Chem. Soc. 1957, 1958.
6. (b) Henbest, H. B. Proc. Chem. Soc. 1963, 159.
7. Bartlett, P. D. Rec. Chem. Prog. 1950, 11, 47.
8. (a) Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
9. (b) Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12, 63.
10. Johnson, M. R.; Kishi, Y. Tetrahedron Lett. 1979, 4347.
11. Chamberlain, P.; Roberts, M. L.; Whitham, G. H. J. Chem. Soc. (B) 1970, 1374.
12. Chautemps, P.; Pierre, J.-L. Tetrahedron 1976, 32, 549.
13. (a) Bach, R. D.; Willis, C. L.; Domagals, J. M. Applications of MO Theory in Organic Chemistry; Csizmadia, I. C., Ed.; Elsevier: Scientific: Amsterdam, 1977; Vol. 2, p 221.
14. (b) Bach, R. D.; Andrés, J. L.; Davis, F. J. Org. Chem. 1992, 57, 613.
15. (a) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrief, H. M. J. Org. Chem. 1996, 61, 1830.
16. (b) Adam, W.; Smerz, A. K. J. Org. Chem. 1996, 61, 3506.
17. Prileschajew, N. Ber. 1909, 42, 481.
18. (a) Lynch, B. M.; Pausacker, K. H. J. Chem. Soc. 1955, 1525.
19. (b) Schwartz, N. N.; Blumbergs, J. H. J. Org. Chem. 1964, 29, 1976.
20. (c) Vilka, M. Bull. Soc. Chim. Fr. 1959, 1401.
21. (d) Renolen, P.; Ugelstad, J. J. Chim. Phys. Phys. Chim. Biol. 1960, 57, 634.
22. (e) House, H. O.; Ro, R. S. J. Am. Chem. Soc. 1958, 80, 2428.
23. (f) Ogata, Y.; Tabushi, I. J. Am. Chem. Soc. 1961, 83, 3440, 3444.
24. (g) Curci, R.; DiPrete, R. A.; Edwards, J. O.; Modena, G. J. Org. Chem. 1970, 35, 740.
25. Berti, G. Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Wiley-Interscience: New York, 1973; Vol. 7, p 93.
26. 14b utilizing gradient geometry optimization.
27. (b) 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.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowki, 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. J. P.; Head-Gordon, M.; González, C.; Pople, J. A. GAUSSIAN 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
28. (c) González, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
29. (d) González, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
30. For a description of the G2 level see: Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
31. (a) Bach, R. D.; Ayala, P. Y.; Schlegel, H. B. J. Am. Chem. Soc. 1996, 118, 12758.
32. (b) Bach, R. D.; Winter, J. E.; Canepa, C.; Blanchette, P. E. J. Org. Chem. 1997, 62, 5191.
33. (c) Bach, R. D.; Owensby, A.; González, C.; Schlegel, H. B. J. Am. Chem. Soc. 1991, 113, 2338.
34. (d) Bach, R. D.; Glukhovtsev, M. N.; Canepa, C. J. Am. Chem. Soc. Submitted for publication.
35. (e) Bach, R. D.; Gonzalez, C.; Glukhovtsev, M. N.; Marquez, M.; Estévez, C. M.; Baboul, A. G.; Schlegel, H. B. J. Phys. Chem. A 1997, 101, 6092.
36. (f) Bach, R. D.; Winter, J. E.; McDouall, J. J. W. J. Am. Chem. Soc. 1995, 117, 8586.
37. (g) Bach, R. D.; Glukhovtsev, M. N.; Gonzalez, C.; Estévez, C. M. Unpublished results.
38. stab = -18.8 kcal/mol. These data are consistent with the observation that protic solvents dramatically slow the rate of alkene epoxidations.
39. 16b the relative stability order is the same. (b) The relative energies of structures B1 and C1 with respect to minima B and C are 7.1 and 8.6 (G2 theory), 8.2 and 7.5 (B3LYP/6-31G(d,p)), and 8.7 and 10.8 kcal/mol (MP2-(full)/6-31G(d,p)), respectively. The energy difference between structures B and A is 1.7 (G2), 1.9 (B3LYP/6-31G(d,p)), and 2.8 kcal/mol (MP2-(full)/6-31G(d,p)).
40. (a) Hunter, E. P.; Lias, G. S. J. Phys. Chem. Ref. Data In press.
41. The value was taken as cited in ref 20b. (b) East, A. L. L.; Smith, B. J.; Radom, L. J. Am. Chem. Soc. 1997, 119, 9014.
42. 20b
43. (b) NIST Standard Reference Database Number 69-February 1997 Release (http://webbook.nist.gov/chemistry).
44. (a) Hart, H. Acc. Chem. Res 1971, 4, 337.
45. (b) Hanzlik, R. P.; Shearer, G. O. J. Am. Chem. Soc. 1975, 106, 1401.
46. (c) Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 55, 117.
47. A cautionary note is in order since the potential energy surface at the MP2/3-21G level was distinctly different from that observed at MP2/ 6-31G(d). An IRC showed that the acidic peroxyformic acid hydrogen migrated to the alcohol oxygen instead of the anticipated intramolecular migration to the carbonyl oxygen.
48. (a) Dryuk, V. G. Russ. Chem. Rev. 1985, 54, 986.
49. (b) DiFuria, F.; Modena, G. Pure Appl. Chem. 1982, 54, 1853.
50. (c) Swern, D. Organic Peroxides; Wiley-Interscience: New York, 1971; Vol. II, pp 73-74 6.
51. (d) For a discussion of solvent assisted proton transfer in alkyl hydrogen peroxides, see: Dankleff, M. A. P.; Ruggero, C.; Edwards, J. O.; Pyun, H. Y. J. Am. Chem. Soc. 1968, 90, 3209.
52. (e) Curci, R.; DiPrete, R. A.; Edwards, J. O.; Modena, G. J. Org. Chem. 1970, 35, 740.
53. (a) Swern, D. J. Am. Chem. Soc. 1947, 69, 1692.
54. (b) The relative rates of epoxidation of ethene, propene, styrene, isobutene, and 2-butene with peracetic acid are 1, 22, 59, 484, and 489, respectively.
55. (a) Yamabe, S.; Kondou, C.; Minato, T. J. Org. Chem. 1996, 61, 616.
56. (b) Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385.
57. 26f local correlation functional.
58. (b) Becke, A. D. Phys. Rev. A 1988, 37, 785.
59. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
60. (d) Stevens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 80, 11623.
61. (e) Lee, C.; Yang, W.; Parr, R. G.; Frisch, M. J. Phys. Rev. 1988, B41, 785.
62. (f) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
63. The stabilization energy for complex 1 computed at the B3LYP/ 6-311G(d,p) level is 10.6 kcal/mol and single point calculations at the QCISD(T) and MP4 level gave energies of 11.1 and 11.4 kcal/mol below that of isolated reactants. The three barrier heights for the oxygen transfer computed relative to these reactant clusters are 18.2, 22.5, and 19.3 kcal/ mol, respectively.