Trifuoroperacetic acid in consecutive Criegee rearrangement and carboxonium ions generation

Arkivoc

Volumn 2005, Issue 4, 2005, Pages 151-171

  Krasutsky, Pavel A ^a   Kolomitsyn, Igor V ^a  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

Author keywords

Baeyer villiger reaction; Carboxonium ion; Criegee rearrangement; Decarboxylation; Oxygen insertion; Peroxide; Trifluoroperacetic acid

Indexed keywords

ACETIC ACID DERIVATIVE; CARBON; FLUORINE DERIVATIVE; ION; PEROXIDE; REAGENT; TRIFLUOROACETIC ACID; TRIFLUOROPERACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DECARBOXYLATION; KINETICS; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 21844470729     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (60)

1. Baeyer, A; Villiger, V. Ber. 1899, 32, 3625.
2. (b) Baeyer, A; Villiger, V. Ber. 1900, 33, 858.
3. Krow, G. R. Org. React. 1993, 43, 251.
4. Mihovilovic, M. D.; Rudroff, F.; Groetzl, B. Current Org. Chem. 2004, 8, 1057.
5. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737.
6. Ogata, Y.; Sawaki, Y. J. Am. Chem. Soc. 1972, 94, 4189.
7. Ogata, Y.; Sawaki, Y. J. Org. Chem. 1972, 37, 2953.
8. Palmer, B. W.; Fry, A. J. Am. Chem. Soc. 1970, 92, 2580.
9. (a) Criegee, R. Chem. Ber. 1944, 77, 722.
10. (b) Criegee, R. Liebigs Ann. Chem. 1948, 560, 127.
11. Deno, N. C. B., Wilbur E.; Kramer, Kenneth E.; Lastomirsky, Robert R. J. Org. Chem. 1970, 35, 3080.
12. Krasutsky, P. A.; Kolomitsyn, I.V.; Kiprof , P.; Carlson, R. M.; Fokin, A. A. J. Org. Chem. 2000, 65, 3926.
13. Hawthorne, M. F.; Emmons, W. D.; McCallum, K. S. J. Am. Chem. Soc. 1958, 80, 6393.
14. Sawaki, Y. in Organic Peroxides. (Ando, W.; Ed.) John Wiley & Sons: New-York. 1992, pp. 425-477.
15. Hedaya, E.; Winstein S. J. Am. Chem. Soc. 1967, 89, 1661.
16. Wistuba, E.; Ruechardt, C. Tetrahedron Lett. 1981, 22, 3389.
17. Langhals, H.; Range, G.; Wistuba, E.; Ruechardt, C. Chem. Ber. 1981, 114, 3813.
18. Ogata, Y.; Tomizawa, K.; Ikeda, T. J. Org. Chem. 1978, 43, 2417.
19. Brink G. J. t.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Rev. 2004, 104, 4105.
20. Krow, G.R. Tetrahedron. 1981, 37, 2697.
21. Goering, H. L.; Olson, A. J. Am. Chem. Soc. 1953, 75, 5853.
22. Krasutsky, P. A.; Kolomitsyn, I.V.; Kiprof, P.; Carlson, R. M.; Sydorenko, N. A., Fokin, A. A. A. J. Org. Chem. 2001, 66, 1701.
23. Olah, G. A.; Laali, K. K.; Wang, Q.; Prakash, G. K. S. Onium Ions; John Willey & Sons: New-York, 1998, pp 269-345.
24. Olah, G. A.; Parker, D. G.; Yoneda, N. Angew. Chem., Int. Ed .Engl. 1978, 17, 909.
25. Olah, G. A.; Parker, D. G.; Yoneda, N. J. Org. Chem. 1977, 42, 32.
26. Hedaya, E.; Winstein S. Tetrahedron Lett. 1962, 563.
27. Gaoni, Y. J. Chem. Soc. C 1968, 2925.
28. Gaoni, Y. J. Chem. Soc. C 1968, 2934.
29. Bailey, W. F.; Shih, M. J. J. Am. Chem. Soc. 1982, 104, 1769.
30. Bailey, W. F.; Bischoff, J. J. J. Org. Chem. 1985, 50, 3009.
31. Marchand, A. P.; Kumar, V. S.; Hariprakasha, H. K. J. Org. Chem. 2001, 66, 2072.
32. (a) Cossy, J.; Ranaivosata, J.-L.; Gille, B.; Belosta, V. Tetrahedron Lett. 1999, 40, 4681.
33. (b) Sugimura, T.; Fujiwara, Y.; Tai, A. Tetrahedron Lett. 1999, 40, 4681.
34. Krasutsky, P. A.; Baula, O. P.; Yurchenko, A. G. Russ. J. Org. Chem. 1994, 30, 370.
35. Krasutsky, P. A.; Baula, O. P.; Botov, E. M. Russ. J. Org. Chem. 1996, 32, 1225.
36. Krasutsky, P. A.; Kolomitsin, I. V.; Carlson, R. M.; Jones, M. Jr. Tetrahedron Lett. 1996, 37, 5673.
37. Kolomitsin, I. V.; Sidorenko, N. A.; Krasutskii, P. A.; Yurchenko, A. G.; Fokin, A. A. Rus. J. Org. Chem. 2000, 36, 438.
38. Krasutsky, P. A.; Kolomitsyn, I. V.; Krasutsky, S. G.; Kiprof, P. Org. Lett. 2004, 6, 2539.
39. Ramsey, B. G.; Taft, R. W. J. Am. Chem. Soc. 1966, 88, 3058.
40. (a) Marchand, A. O.; Kumar, S.; Hariprakasha, H. K. J. Org. Chem. 2001, 66, 2072.
41. (b) Wishnok, J. S.; Schleyer, P. von R.; Funke, E.; Pandit, G. D.; Williams, R. O.; Nickon, A. J. Org. Chem. 1973, 38, 539.
42. (c) Black, R. M.; Gill, G. B.; Hands, D. J. Chem Soc. Chem Commun. 1972, 31.
43. (d) Fish, M; Smallcombe, S.; Gramain, J. C.; McKervey, M. A.; Anderson, J. E. J. Org. Chem. 1970, 35, 1886.
44. (f) Steter, H.; Tacke, P. Chem. Ber. 1963, 96, 694.
45. Reyes, L.; Castro, M.; Cruz, J.; Rubio, M. J. Phys. Chem. A 2005, 109, 3383.
46. Larsen, J. W.; Bouis, P. A.; Riddle, C. A. J. Org. Chem. 1980, 45, 4969.
47. For references on the decrease in stabilities of triaryloxycarbenium ions compare to trialkoxycarbenium ions see: (a) Kandanarachchi, P.; Sinnott, M. L. J. Am. Chem. Soc. 1994, 116, 5592.
48. (b) Kandanarachchi, P.; Sinnott, M. L. J. Am. Chem. Soc. 1994, 116, 5601.
49. (c) Kandanarachchi, P.; Sinnott, M. L. J. Chem. Soc., Chem. Commun. 1992, 777.
50. Krasutsky, P. A.; Kolomitsyn, I. V.; Botov, E. M.; Carlson, R. M.; Semenova, I. G.; Fokin, A. A. Tetrahedron Lett. 2002, 43, 8687.
51. Krasutsky, P. A.; Semenova, I. G., Safronova, E. E.; Novikova, M. I., Yurchenko, A. G. Zh. Org. Khimii. 1989, 25, 11, 2336.
52. This ratio of trifluoroacetates is expected for nucleophilic trapping of 3-homoadamantyl cation (94:6 for the reaction with acetate ion): Nordlander, J. E.; Jindal, S. P.; Schleyer, P. v. R.; Fort, Jr., R. C.; Harper, J. J.; Nicholas, R. D. J. Am. Chem. Soc. 1966, 89, 4475.
53. Liggero, S. H.; Sustmann, R.; Schleyer, P. v. R. J. Amer. Chem. Soc. 1969, 91, 4571.
54. Krapcho, A. P.; Johanson, R. G. J. Org. Chem. 1971, 36, 146.
55. Krasutsky, P. A.; Kolomitsyn, I. V.; Carlson, R. M. Org. Lett. 2001, 3, 2997.
56. Krasutsky, P.A.; Kolomitsyn, I. V.; Carlson, R.; Hong, W. U.S. Patent Application June 5, 2002, Serial No. 10/163,840.
57. Krasutsky, P.A.; Kolomitsyn, I. V.; Carlson, R.; Hong, W. PCT Int. Appl. 2002,CODEN: PIXXD2 WO 2002098924 A2 20021212, 24 pp.
58. Sawada, H. Chem. Rev. 1996, 96, 1779.
59. Sawada, H. J. Fluorine Chem. 2000, 105, 219.
60. Sawada, H.; Kita, M.; Yoshimizu, J.; Kyokane, T.; Kawase, Y.; Hayakawa, K.; Yoshino, J. J. Fluorine Chem. 1997, 92, 51.