Selectivities in the oxidation of tertiary amines and pyridine derivatives by perfluoro cis-2,3-dialkyloxaziridines

Tetrahedron

Volumn 54, Issue 27, 1998, Pages 7831-7842

  Arnone, Alberto ^a   Metrangolo, Pierangelo ^a   Novo, Barbara ^a   Resnati, Giuseppe ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DEXTROMETHORPHAN; LIDOCAINE; OXAZORIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; OXIDATION; POLYAMINE METABOLISM; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032474725     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00417-7     Document Type: Article

References (71)

1. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
2. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
3. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
4. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
5. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
6. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
7. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
8. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
9. 1. Schmitz, E. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Ed.; Pergamon Press: Oxford, 1984, vol. 7, p 204. Andreae, S.; Schmitz, E. Synthesis 1991, 327. Schmitz, E.; Ohme, R.; Schramm, S.; Striegler, H.; Heyne, H.-U.; Rusche, J. J. Prakt. Chem. 1977, 195. Schmitz, E.; Ohme, R.; Schramm, S. Liebigs Ann. Chem. 1967, 702, 131. Schmitz, E.; Ohme, R.; Schramm, S. Chem. Ber. 1964, 2521. Hata, Y.; Watanabe, M. J. Am. Chem. Soc 1979, 101, 6671. Hata, Y.; Watanabe, M. J. Org. Chem. 1981, 46, 610. Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791. Vidal, J.; Damestoy, S., Collet, A. Tetrahedron Lett. 1995, 36, 1439.
10. Niederer, D. A.; Kapron, J. T.; Vederas, J. C. Tetrahedron Lett. 1993, 34, 6859.
11. 2. Haddadin, M. J.; Freeman, J. P. in Heterocyclic Compounds; Hassner, A. Ed.; John Wiley & Sons: New York, 1985, vol. 42, p. 325. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J.; Lagowski, J. M. Eds.; Academic Press; New York, 1963, vol. 2 p. 83. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J. Eds., Academic Press: New York, 1979, vol. 24, p. 63 Boyd, D. R.; Jennings, W. B.; McGuckin, R. M.; Rutherford, M.; Saket, B. M. J. Chem. Soc., Chem. Commun. 1985, 582 Hanquet, G.; Lusinchi, X. Tetrahedron Lett. 1993, 34, 5299. Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron Lett. 1988, 29, 3941.
12. 2. Haddadin, M. J.; Freeman, J. P. in Heterocyclic Compounds; Hassner, A. Ed.; John Wiley & Sons: New York, 1985, vol. 42, p. 325. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J.; Lagowski, J. M. Eds.; Academic Press; New York, 1963, vol. 2 p. 83. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J. Eds., Academic Press: New York, 1979, vol. 24, p. 63 Boyd, D. R.; Jennings, W. B.; McGuckin, R. M.; Rutherford, M.; Saket, B. M. J. Chem. Soc., Chem. Commun. 1985, 582 Hanquet, G.; Lusinchi, X. Tetrahedron Lett. 1993, 34, 5299. Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron Lett. 1988, 29, 3941.
13. 2. Haddadin, M. J.; Freeman, J. P. in Heterocyclic Compounds; Hassner, A. Ed.; John Wiley & Sons: New York, 1985, vol. 42, p. 325. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J.; Lagowski, J. M. Eds.; Academic Press; New York, 1963, vol. 2 p. 83. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J. Eds., Academic Press: New York, 1979, vol. 24, p. 63 Boyd, D. R.; Jennings, W. B.; McGuckin, R. M.; Rutherford, M.; Saket, B. M. J. Chem. Soc., Chem. Commun. 1985, 582 Hanquet, G.; Lusinchi, X. Tetrahedron Lett. 1993, 34, 5299. Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron Lett. 1988, 29, 3941.
14. 2. Haddadin, M. J.; Freeman, J. P. in Heterocyclic Compounds; Hassner, A. Ed.; John Wiley & Sons: New York, 1985, vol. 42, p. 325. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J.; Lagowski, J. M. Eds.; Academic Press; New York, 1963, vol. 2 p. 83. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J. Eds., Academic Press: New York, 1979, vol. 24, p. 63 Boyd, D. R.; Jennings, W. B.; McGuckin, R. M.; Rutherford, M.; Saket, B. M. J. Chem. Soc., Chem. Commun. 1985, 582 Hanquet, G.; Lusinchi, X. Tetrahedron Lett. 1993, 34, 5299. Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron Lett. 1988, 29, 3941.
15. 2. Haddadin, M. J.; Freeman, J. P. in Heterocyclic Compounds; Hassner, A. Ed.; John Wiley & Sons: New York, 1985, vol. 42, p. 325. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J.; Lagowski, J. M. Eds.; Academic Press; New York, 1963, vol. 2 p. 83. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J. Eds., Academic Press: New York, 1979, vol. 24, p. 63 Boyd, D. R.; Jennings, W. B.; McGuckin, R. M.; Rutherford, M.; Saket, B. M. J. Chem. Soc., Chem. Commun. 1985, 582 Hanquet, G.; Lusinchi, X. Tetrahedron Lett. 1993, 34, 5299. Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron Lett. 1988, 29, 3941.
16. 2. Haddadin, M. J.; Freeman, J. P. in Heterocyclic Compounds; Hassner, A. Ed.; John Wiley & Sons: New York, 1985, vol. 42, p. 325. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J.; Lagowski, J. M. Eds.; Academic Press; New York, 1963, vol. 2 p. 83. Schmitz, E. in Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J. Eds., Academic Press: New York, 1979, vol. 24, p. 63 Boyd, D. R.; Jennings, W. B.; McGuckin, R. M.; Rutherford, M.; Saket, B. M. J. Chem. Soc., Chem. Commun. 1985, 582 Hanquet, G.; Lusinchi, X. Tetrahedron Lett. 1993, 34, 5299. Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron Lett. 1988, 29, 3941.
17. 3. (a) Sekiya, A.; DesMarteau, D. D. J. Org. Chem. 1979, 44, 1131.
18. (b) Sekiya, A.; DesMarteau, D D. Inorg. Chem. 1979, 18, 919.
19. (c) Petrov, V. A.; DesMarteau, D. D. J. Chem. Soc., Perkin Trans. 1 1993, 505.
20. 4 Sekiya, A.; DesMarteau, D. D. J. Fluorine Chem. 1979, 14, 289.
21. 5 (a) Balsarini, C.; Novo, B.; Resnati, G. J. Fluorine Chem. 1996, 80, 31.
22. (b) Bernardi, R.; Novo, B.; Resnati, G. J. Chem. Soc., Perkin Trans. 1 1996, 2517.
23. (c) Bragante, L.; DesMarteau, D. D. J. Fluorine Chem. 1991, 53, 181.
24. 6. (a) Albini, A. Synthesis 1993, 263.
25. (b) Rousselet, G.; Chassagnard, C.; Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1996, 37, 8497.
26. (c) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199.
27. (d) Kilenyi, S. N. Oxidation of Carbon-Halogen Bonds in Comprehensive Organic Synthesis, Trost, B. M. and Fleming, I. Eds., Pergamon Press, Oxford, 1991, vol. 7, pp. 661-662.
28. 7. Albini, A. Heterocycles 1992, 34, 1973.
29. 8. Gilchrist, T. L. Oxidation of Nitogen and Phosphorous in Comprehensive Organic Synthesis, Trost, B. M. and Fleming, I. Eds., Pergamon Press, Oxford, 1991, vol. 7, pp. 748-749. Malpass, J. R. Aliphatic, Acyclic, and Cyclic Amines in Comprehensive Organic Chemistry, Barton, D. and Ollis, W. D. Eds., Pergamon Press, Oxford, 1979, pp. 201-204 Challis, B. C.; Butler, A. R. Substitution at an Amino Nitrogen in The Chemistry of the Amino Group, Patai, S. Ed., Interscience Publisher, John Wiley & Sons, London, 1968, pp. 326-338.
30. 8. Gilchrist, T. L. Oxidation of Nitogen and Phosphorous in Comprehensive Organic Synthesis, Trost, B. M. and Fleming, I. Eds., Pergamon Press, Oxford, 1991, vol. 7, pp. 748-749. Malpass, J. R. Aliphatic, Acyclic, and Cyclic Amines in Comprehensive Organic Chemistry, Barton, D. and Ollis, W. D. Eds., Pergamon Press, Oxford, 1979, pp. 201-204 Challis, B. C.; Butler, A. R. Substitution at an Amino Nitrogen in The Chemistry of the Amino Group, Patai, S. Ed., Interscience Publisher, John Wiley & Sons, London, 1968, pp. 326-338.
31. 8. Gilchrist, T. L. Oxidation of Nitogen and Phosphorous in Comprehensive Organic Synthesis, Trost, B. M. and Fleming, I. Eds., Pergamon Press, Oxford, 1991, vol. 7, pp. 748-749. Malpass, J. R. Aliphatic, Acyclic, and Cyclic Amines in Comprehensive Organic Chemistry, Barton, D. and Ollis, W. D. Eds., Pergamon Press, Oxford, 1979, pp. 201-204 Challis, B. C.; Butler, A. R. Substitution at an Amino Nitrogen in The Chemistry of the Amino Group, Patai, S. Ed., Interscience Publisher, John Wiley & Sons, London, 1968, pp. 326-338.
32. 9. Zajac, W. W. Jr.; Walters, T. R.; Darcy, M. G. J. Org. Chem. 1988, 53, 5856.
33. 10. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
34. 11. Lidocaine N-oxide 3g is one of the lidocaine metabolites: Patterson, L. H.; Hall, G.; Nijjar, B. S.; Khatra, P. K. Cowan, D. A. J. Pharm. Pharmacol. 1986, 38, 326.
35. 12. Also brucine N-oxide 3h has been found in some Strychnos species (Bisset, N. G.; Choudhury, A. K. Phytochemistry 1974, 13, 259, ibid. 1974, 13, 265) , but the compound may be formed during extraction processes (Cai, B.-C., Hattori, M.; Namba, T. Chem. Pharm. Bull. 1990, 38, 1295).
36. 12. Also brucine N-oxide 3h has been found in some Strychnos species (Bisset, N. G.; Choudhury, A. K. Phytochemistry 1974, 13, 259, ibid. 1974, 13, 265) , but the compound may be formed during extraction processes (Cai, B.-C., Hattori, M.; Namba, T. Chem. Pharm. Bull. 1990, 38, 1295).
37. 12. Also brucine N-oxide 3h has been found in some Strychnos species (Bisset, N. G.; Choudhury, A. K. Phytochemistry 1974, 13, 259, ibid. 1974, 13, 265) , but the compound may be formed during extraction processes (Cai, B.-C., Hattori, M.; Namba, T. Chem. Pharm. Bull. 1990, 38, 1295).
38. 13. Haloperidol N-Oxide 3k is one of the haloperidol metabolites: Tomlinson, A. J.; Benson, L. M.; Johnson, K. L.; Naylor, S. J. Chromatography, Biomed. Appl. 1993, 621, 239.
39. 14. Cook, M. J.; Katritzky, A. R.; Moreno Manas M. J. Chem. Soc. (B) 1971, 1330.
40. 15. Cymerman Craig, J.; Purushothaman, K. K. J. Org. Chem. 1970, 35, 1721.
41. 16. Cope, A C.; Trumbull, E. R. Organic React. 1960, 11, 319.
42. 17. Srebnik, M.; Mechoulam, R. Synthesis 1983, 1046.
43. 18. Arnone, A.; Bernardi, R.; Cavicchioli, M.; Resnati, G. J. Org. Chem. 1995, 60, 2314.
44. 19. Arnone, A.; DesMarteau, D.D.; Novo, B.; Petrov, V.A.; Pregnolato, M.; Resnati, G. J. Org. Chem. 1996, 61, 8805.
45. 20. Approaches related to that described in this paper for diverting to carbon sites electrophilic oxidations of unsaturated amines: (a) Asensio, G.; Mello, R.; Boix-Bernardini, C.; González-Nuñez, M.E.; Castellano, G. J. Org. Chem. 1995, 60, 3692.
46. (b) Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A.; Diez, A.; Rubiralta, M. J. Chem. Soc., Chem. Commun. 1995, 293;
47. (c) Asensio, G.; González-Nuñez, M.E.; Boix-Bernardini, C.; Mello, R.; Adam, W. J. Am. Chem. Soc. 1993, 115, 7250.
48. 21. Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. Tetrahedron Lett. 1992, 33, 7245. DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M,; Resnati, G. J. Org. Chem. 1994, 59, 2762. Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 55, 6329. Cavicchioli, M.; Mele, A.; Montanari, V.; Resnati, G. J. Chem. Soc., Chem. Commun. 1995, 901.
49. 21. Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. Tetrahedron Lett. 1992, 33, 7245. DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M,; Resnati, G. J. Org. Chem. 1994, 59, 2762. Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 55, 6329. Cavicchioli, M.; Mele, A.; Montanari, V.; Resnati, G. J. Chem. Soc., Chem. Commun. 1995, 901.
50. 21. Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. Tetrahedron Lett. 1992, 33, 7245. DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M,; Resnati, G. J. Org. Chem. 1994, 59, 2762. Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 55, 6329. Cavicchioli, M.; Mele, A.; Montanari, V.; Resnati, G. J. Chem. Soc., Chem. Commun. 1995, 901.
51. 21. Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. Tetrahedron Lett. 1992, 33, 7245. DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M,; Resnati, G. J. Org. Chem. 1994, 59, 2762. Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 55, 6329. Cavicchioli, M.; Mele, A.; Montanari, V.; Resnati, G. J. Chem. Soc., Chem. Commun. 1995, 901.
52. 21. Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. Tetrahedron Lett. 1992, 33, 7245. DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M,; Resnati, G. J. Org. Chem. 1994, 59, 2762. Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 55, 6329. Cavicchioli, M.; Mele, A.; Montanari, V.; Resnati, G. J. Chem. Soc., Chem. Commun. 1995, 901.
53. 21. Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. Tetrahedron Lett. 1992, 33, 7245. DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M,; Resnati, G. J. Org. Chem. 1994, 59, 2762. Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 55, 6329. Cavicchioli, M.; Mele, A.; Montanari, V.; Resnati, G. J. Chem. Soc., Chem. Commun. 1995, 901.
54. 22. Traces of N-oxide-epoxide products (<6%) were also present.
55. 23. Mosher, H. S.; Turner, L.; Carlsmith, A. Org. Synthesis 1953, 33, 79.
56. 24. Petrowitsch, T.; Eilbracht P. Synlett 1997, 287.
57. 25. O'Neil, I. A.; Miller, N. D.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1995, 619. O'Neil, I. A.; Miller, N. D.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1995, 617. O'Neil, I. A; Miller, N. D.; Peake, J.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1993, 515.
58. 25. O'Neil, I. A.; Miller, N. D.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1995, 619. O'Neil, I. A.; Miller, N. D.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1995, 617. O'Neil, I. A; Miller, N. D.; Peake, J.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1993, 515.
59. 25. O'Neil, I. A.; Miller, N. D.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1995, 619. O'Neil, I. A.; Miller, N. D.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1995, 617. O'Neil, I. A; Miller, N. D.; Peake, J.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1993, 515.
60. 26. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. Synlett 1997, 322. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1005. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1001. Reetz, R. T.; Lauterbach, E. H. Tetrahedron Lett. 1991, 32, 4481. Yamamoto, Y.; Oda, J.; Inouye, Y. J. Org. Chem. 1976, 41, 303. Enders, D.; Kempen, H. Synlett 1994, 969.
61. 26. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. Synlett 1997, 322. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1005. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1001. Reetz, R. T.; Lauterbach, E. H. Tetrahedron Lett. 1991, 32, 4481. Yamamoto, Y.; Oda, J.; Inouye, Y. J. Org. Chem. 1976, 41, 303. Enders, D.; Kempen, H. Synlett 1994, 969.
62. 26. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. Synlett 1997, 322. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1005. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1001. Reetz, R. T.; Lauterbach, E. H. Tetrahedron Lett. 1991, 32, 4481. Yamamoto, Y.; Oda, J.; Inouye, Y. J. Org. Chem. 1976, 41, 303. Enders, D.; Kempen, H. Synlett 1994, 969.
63. 26. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. Synlett 1997, 322. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1005. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1001. Reetz, R. T.; Lauterbach, E. H. Tetrahedron Lett. 1991, 32, 4481. Yamamoto, Y.; Oda, J.; Inouye, Y. J. Org. Chem. 1976, 41, 303. Enders, D.; Kempen, H. Synlett 1994, 969.
64. 26. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. Synlett 1997, 322. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1005. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1001. Reetz, R. T.; Lauterbach, E. H. Tetrahedron Lett. 1991, 32, 4481. Yamamoto, Y.; Oda, J.; Inouye, Y. J. Org. Chem. 1976, 41, 303. Enders, D.; Kempen, H. Synlett 1994, 969.
65. 26. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. Synlett 1997, 322. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1005. Davies, S.; G.; Smyth, G. D. Tetrahedron: Asymm. 1996, 7, 1001. Reetz, R. T.; Lauterbach, E. H. Tetrahedron Lett. 1991, 32, 4481. Yamamoto, Y.; Oda, J.; Inouye, Y. J. Org. Chem. 1976, 41, 303. Enders, D.; Kempen, H. Synlett 1994, 969.
66. 27. DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897. Arnone, A.; Cavicchioli, M.; Montanari, V.; Resnati, G. J. Org. Chem. 1994, 59, 5511.
67. 27. DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897. Arnone, A.; Cavicchioli, M.; Montanari, V.; Resnati, G. J. Org. Chem. 1994, 59, 5511.
68. 28. Novo, B.; Resnati, G; Bégué, J-P. M'Bida, A.; Bonnet-Delpon, D. Synthesis 1996, 399. DesMarteau, D. D.; Petrov, V.A.; Montanari, V.; Pregnolato, M.; Resnati, G. J. Org. Chem. 1994, 59, 2762.
69. 28. Novo, B.; Resnati, G; Bégué, J-P. M'Bida, A.; Bonnet-Delpon, D. Synthesis 1996, 399. DesMarteau, D. D.; Petrov, V.A.; Montanari, V.; Pregnolato, M.; Resnati, G. J. Org. Chem. 1994, 59, 2762.
70. 29. Kenyon, G. L.; Eargle, D. H. Jr.; Koch, C. W. J. Org. Chem. 1976, 41, 2417. Bravo, R.; Laurent, J.-P. J. Chem. Research (M). 1983, 710.
71. 29. Kenyon, G. L.; Eargle, D. H. Jr.; Koch, C. W. J. Org. Chem. 1976, 41, 2417. Bravo, R.; Laurent, J.-P. J. Chem. Research (M). 1983, 710.