Regioselective radical cyclization initiated by the reaction of allylic hydroperoxides with iron(II) sulfate

Tetrahedron

Volumn 59, Issue 3, 2003, Pages 353-366

  Masuyama, Araki ^a   Sugawara, Tomohiro ^a   Nojima, Masatomo ^a   McCullough, Kevin J ^b  

^a OSAKA UNIVERSITY   (Japan)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

Allylic hydroperoxide; endo trig radical cyclization; Iron(II) sulfate; Ring enlargement

Indexed keywords

1 (1 CHLOROCYCLOHEXYL)ETHANONE; 1 METHYL 2 METHYLENE 1 CYCLOHEXYLHYDROPEROXIDE; COPPER CHLORIDE; FERROUS SULFATE; HYDROPEROXIDE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; DECOMPOSITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0037434002     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01522-3     Document Type: Article

References (66)

1. (a) Beckwith A.L.J. Tetrahedron. 37:1981;3073.
2. (b) Ramaiah M. Tetrahedron. 43:1987;3541.
3. (c) Curran D.P. Trost B.M. Comprehensive Organic Chemistry. Vol. 4:1991;779-831 Pergamon, Oxford.
4. (d) Thebtaranonth C., Thebtaranonth Y. Cyclization Reactions. 1994;CRC, Boca Raton, FL. pp 77-167.
5. (e) Fossey J., Lefort D., Sorba J. Free Radicals in Organic Chemistry. 1995;Wiley, Chichester. Chapter 13, pp 151-165.
6. (f) Giese B., Kopping B., Göbel T., Dickhaut J., Thoma G., Kulicke K.J., Trach F. Org. React. 48:1996;301.
7. (g) Handa S., Pattenden G. Contemp. Org. Synth. 4:1997;19.
8. (h) Yet L. Tetrahedron. 55:1999;9349.
9. (a) Russel G.A., Li C. Tetrahedron Lett. 37:1996;2557.
10. (b) Chang S.-Y., Jiaang W.-T., Cherng C.-D., Tand K.-H., Huang C.-H., Tsai Y.-M. J. Org. Chem. 62:1997;9089.
11. (c) Ishibashi H., Higuchi M., Ohba M., Ikeda M. Tetrahedron Lett. 39:1998;75.
12. (d) Handa S., Pattenden G., Li W.-S. Chem. Commun. 1998;311.
13. (e) Lee E., Yoon C.H., Lee T.H., Kim S.Y., Ha T.J., Sung Y.-S., Park S.-H., Lee S. J. Am. Chem. Soc. 120:1998;7469.
14. (f) Parsons A.F., Williams D.A.J. Tetrahedron. 54:1998;13405.
15. (g) Della E.W., Kostakis C., Smith P.A. Org. Lett. 1:1999;363.
16. (h) Clark A.J., Dell C.P., Ellard J.M., Hunt N.A., McDonagh J.P. Tetrahedron Lett. 40:1999;8619.
17. Nonami Y., Baran J., Sosnicki J., Mayr H., Masuyama A., Nojima M. J. Org. Chem. 64:1999;4060.
18. (a) Dussault P.H. Foote C.S., Valentine J.S., Greenberg A., Liebman J.F. Active Oxygen in Chemistry. Vol. 2:1995;141-203 Blackie, London. Chapter 5.
19. (b) McCullough K.J., Motomura Y., Masuyama A., Nojima M. Chem. Commun. 1998;1173. and references therein.
20. (a) Wasserman H.H., Murray R.W. Singlet Oxygen. 1979;Academic, New York. Chapter 8, pp 287-427.
21. (b) Frimer A.A. Chem. Rev. 79:1979;359.
22. (c) Foote C.S., Clennan E.L. Foote C.S., Valentine J.S., Greenberg A., Liebman J.F. Active Oxygen in Chemistry. Vol. 2:1995;116-117 Blackie, London. Chapter 4.
23. (d) Stratakis M., Orfanopoulos M. Tetrahedron. 56:2000;1595.
24. Porter N.A. Ando W. Organic Peroxides. 1992;107-111 Wiley, New York. Chapter 2.
25. (a) Bartlett P.D., Mendenhall G.D. J. Am. Chem. Soc. 92:1970;210.
26. (b) Kopecky K.R., Scott W.A., Lockwood P.A., Mumford C. Can. J. Chem. 56:1978;1114.
27. (c) Mori A., Abe M., Nojima M. J. Org. Chem. 66:2001;3548. and references therein.
28. Giese B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds. 1986;Pergamon, Oxford. Chapter 2.
29. (a) Galatsis P., Scott D.M., Faber T. J. Org. Chem. 58:1993;1215.
30. (b) Afzal M., Walton J.C. J. Chem. Soc., Perkin Trans. 2. 1999;937.
31. (a) Molander G.A., McKie J.A. J. Org. Chem. 59:1994;3186.
32. (b) Molander G.A. Acc. Chem. Res. 31:1998;603.
33. (c) Jung M.E. Synlett. 1999;843.
34. Beckwith A.L.J., Zimmermann J. J. Org. Chem. 56:1991;5791-5796.
35. Galli C., Giovannelli G., Illuminati G., Mandolini L. J. Org. Chem. 44:1979;1258.
36. (a) Beckwith A.L.J., Drok K., Maillard B., Degueil-Castaing M., Philippon A. Chem. Commun. 1997;499.
37. (b) Philippon A., Degueil-Castaing M., Beckwith A.L.J., Maillard B. J. Org. Chem. 63:1998;6814.
38. Willmore N.D., Goodman R., Lee H.-H., Kennedy R.M. J. Org. Chem. 57:1992;1216.
39. Kaiser, E. M.; Benkeser, R. A. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 852-855.
40. Turro, N. J.; Leersmakers, P. A.; Vesley, G. F. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, pp 297-299.
41. (a) Ando W., Sekiguchi A., Ogiwara J., Migita T. J. Chem. Soc., Chem. Commun. 1975;145.
42. (b) Baldwin J.E., Adlington R.M., Bottaro J.C., Kolhe J.N., Newington I.M., Perry M.W.D. Tetrahedron. 42:1986;4235.
43. (a) Willhalm B., Thomas A.F. Helv. Chim. Acta. 50:1967;383.
44. (b) Baldwin J.E., Lever O.W. Jr. J. Chem. Soc., Chem. Commun. 1973;343.
45. (c) Bardyshev I.I., Buinova E.F., Protaswhchik I.V. Zh. Org. Khim. 7:1971;2307. Chem. Abstr. 1972, 76, 46311.
46. (c) Bardyshev I.I., Buinova E.F., Protaswhchik I.V. Zh. Org. Khim. 7:1971;2307. Chem. Abstr. 1972, 76, 46311.
47. (d) Corey E.J., Kwiatkowski G.T. J. Am. Chem. Soc. 88:1966;5654.
48. (e) Marshall J.A., Bierebaum R. J. Org. Chem. 42:1977;3309.
49. (f) Posner G.H., Shulman-Roskes E.M., Oh C.H., Carry J.C., Green J.V., Clark A.B., Dai H.A., Anjeh E.N. Tetrahedron Lett. 32:1991;6489.
50. (g) Bowden, R. D. 4-Substituted Tetrahydropyrans. Ger. Offen. DE 1941010, March 5, 1970.
51. (h) Posner G.H., Loomies G.L., Sawaya H.S. Tetrahedron Lett. 1975;1373.
52. (i) McMurry J.E., Krepski L.R. J. Org. Chem. 41:1976;3929.
53. (j) Hara S., Taguchi H., Yamamoto H., Nozaki H. Tetrahedron Lett. 1975;1545.
54. (k) Woodworth C.W., Buss V., Schleyer P.R. J. Chem. Soc., Chem. Commun. 1968;569.
55. (l) Adam W., Encarnacion L.A.A. Chem. Ber. 115:1982;2592.
56. (a) Danheiser R.L., Nowick J.S. J. Org. Chem. 56:1991;1176.
57. (b) Wedler C., Kunath A., Schick H. J. Org. Chem. 60:1995;758.
58. (a) Kopecky K.R., Filby J.E., Mumford C., Lockwood P.A., Ding J.-Y. Can. J. Chem. 58:1975;1103.
59. (b) Shimizu N., Bartlett P.D. J. Am. Chem. Soc. 98:1976;4193.
60. (c) Paquette L.A., Liotta D.C. Tetrahedron Lett. 1976;2681.
61. (d) Leclercq D., Bats J.-P., Picard P., Moulines J. Synthesis. 1982;778.
62. (e) Dussault P.H., Woller K.R. J. Org. Chem. 62:1997;1556.
63. (f) Davies A.G., Davison I.G.E., Schiesser C.H. J. Chem. Soc., Chem. Commun. 1989;742.
64. (g) McGoran E.C., Wyborney M. Tetrahedron Lett. 30:1989;783.
65. Reutrakul V., Nimgirawath S., Panichanun S., Srikirin Y. Tetrahedron Lett. 1979;1321.
66. Sheldrick, G. M. SHELXTL PC (Vers. 5.1); Brucker AXS: Madison,WI, USA.