Chemistry of dioxine-annelated cycloheptatriene endoperoxides and their conversion into tropolone derivatives: an unusual non-benzenoid singlet oxygen source

Tetrahedron

Volumn 62, Issue 17, 2006, Pages 4003-4010

  Daştan, Arif ^a   Balci, Metin ^b  

^a ATATÜRK UNIVERSITY   (Turkey)

^b MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Endoperoxide; Rearrangement; Singlet oxygen; Tropolone; Tropone

Indexed keywords

AROMATIC COMPOUND; DIOXIN; ENDOPEROXIDE; KETONE; OXYGEN; THIOUREA; TROPOLONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PHOTOOXIDATION; PRIORITY JOURNAL;

EID: 33646168563     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.026     Document Type: Article

References (65)

1. Banwell M.G. Aust. J. Chem. 44 (1991) 1-36
2. Asao T., and Oda M. In: Regitz M. (Ed). Methoden der Organischen Chemie Houben Weyl Vol. 5/2c (1985), George Thieme, Stuttgart 710-768
3. Pietra F. Acc. Chem. Res. 12 (1979) 132-138
4. Pietra F. Chem. Rev. 73 (1973) 293-364
5. Piettre S.R., Ganzhorn A., Hoflsack J., Islam K., and Hornsperger J.M. J. Am. Chem. Soc. 9 (1997) 3201-3204
6. Piettre S.R., Andre C., Chanal M.C., Ducep J.B., Lesur B., Piriou F., Raboisson P., Rondeau J.M., Schelcher C., Zimmermann P., and Ganzhorn A.J. J. Med. Chem. 40 (1997) 4208-4221
7. Tomita K., Hoshino Y., Nakakita Y., Umezewa S., Miyaki T., Oki T., and Kawaguchi H. J. Antibiot. 42 (1989) 317-321
8. Banwell M.G., Corbett M., Mackay M.F., and Richards S.L. J. Chem. Soc., Perkin Trans. 1 11 (1992) 1329-1334
9. Kamei, H.; Ohbayashi, M.; Tomita, K.; Sugawara, K.; Konishi, M.; U.S. (1989), 8 pp. CODEN: USXXAM US 4833079 A 19890523 CAN 111193069 AN 1989:593069.
10. Saleh N.A., Zfiefak A., Mordarski M., and Pulverer G. Zbl. Bakt. Hyg. A 270 (1988) 160-170
11. Suziki H., Ueda T., Juranek I., Yamamoto S., Katoh T., Node M., and Suziki T. Biochem. Biophys. Res. commun. 275 (2000) 885-889
12. Kitamura S., Iida T., Shiarata K., and Kase H. J. Antibiot. 39 (1986) 589-593
13. Soung M.-G., Matsui M., and Kitahara T. Tetrahedron 56 (2000) 7741-7745
14. Boger D.L., Ichikawa S., and Jiang H. J. Am. Chem. Soc. 122 (2000) 12169-12173
15. Lee J.C., Jin S.-J., and Cha J.K. J. Org. Chem. 63 (1998) 2804-2805
16. Miyashita M., Hara S., and Yoshikoshi A. J. Org. Chem. 52 (1987) 2602-2604
17. (e) Nozoe, T. Sci Repts. Tokohu Univ., First Ser. 1950, 34, 199-236.
18. (f) Nozoe, T. Nature (London) 1951, 167, 1055-1057.
19. Erdtman H., and Gripenberg J. Acta Chem. Scand. 2 (1948) 625-638
20. Gripenberg J. Acta Chem. Scand. 2 (1948) 639-646
21. Anderson A.B., and Sheerard E.C. J. Am. Chem. Soc. 55 (1933) 3813-3819
22. Scott A.I., and Lee E. J. Chem. Soc., Chem. Commun. (1972) 655-656
23. Scott A.I., and Weisner K.J. J. Chem. Soc., Chem. Commun. (1972) 1075-1077
24. Scott A.I., Guilford H., and Lee E. J. Am. Chem. Soc. 93 (1971) 3534-3536
25. Johns R.B., Johnson A.W., and Murray J. J. Chem. Soc., Chem. Commun. (1954) 2352-2356
26. Bartels-Keith J.R., Johnson A.W., and Taylor W.I. J. Chem. Soc., Chem. Commun. (1951) 198-202
27. Asao T., Yahigara M., and Kitahara Y. Bull. Chem. Soc. Jpn. 51 (1978) 2131-2135
28. Oda M., and Kitahara M. Tetrahedron Lett. (1969) 3295-3296
29. Daştan A., Yildiz Y.K., Kazaz C., and Balci M. Turk. J. Chem. 26 (2002) 143-151
30. Daştan A., Yildiz Y.K., and Balci M. Synth. Commun. 31 (2001) 3807-3815
31. Shono T., Nozoe T., Maekava H., and Kashimura S. Tetrahedron Lett. 29 (1988) 555-558
32. Ikeda Y., Mori A., and Takeshita H. Bull. Chem. Soc. Jpn. 66 (1993) 2779-2780
33. Takeshita H., Mori A., and Suizi H. Bull. Chem. Soc. Jpn. 60 (1987) 1429-1432
34. Takeshita H., Mori A., Kusaba T., and Watanabe H. Bull. Chem. Soc. Jpn. 60 (1987) 4325-4333
35. Balci M. Chem. Rev. 81 (1981) 91-108
36. Daştan A., Saracoglu N., and Balci M. Eur. J. Org. Chem. (2001) 3519-3522
37. Güney M., Daştan A., and Balci M. Helv. Chim. Acta 88 (2005) 830-838
38. Güney M., Çelik Z.C., Daştan A., and Balci M. Can. J. Chem. 83 (2005) 227-235
39. Fukunaga T., and Simmons H.E. J. Am. Chem. Soc. 89 (1967) 5208-5215
40. Fukunaga T., Mukai T., Akasaki Y., and Suzuki R. Tetrahedron Lett. (1970) 2975-2978
41. Shono T., Nozoe T., Maekawa H., and Kashimura S. Tetrahedron Lett. 29 (1988) 555-558
42. Mori A., Kubo K., and Takeshita H. Bull. Chem. Soc. Jpn. 66 (1993) 3742-3746
43. Mori A., and Takeshita H. Kyushu Daigaku Sogo Rikogaku Kenkyuka Hokoku 3 (1981) 125-130
44. Adam W. In: Patai S. (Ed). The Chemistry of Peroxide (1983), Wiley, New York 829
45. Adam W., Heil M., Mosandl T., and Saha-Möller C.R. In: Ando W. (Ed). Organic Peroxides (1992), Wiley, New York 221
46. 2 Vol. 2 (1985), CRC, Florida 37
47. Murray R.W., and Jeyeraman R. J. Org. Chem. 50 (1985) 2847-2853
48. Murray R.W. Chem. Rev. 89 (1989) 1187-1201
49. Adam W., and Hadjiarapoglou L. Top. Curr. Chem. 164 (1993) 45-62
50. Kornblum N., and De La Mare H.E. J. Am. Chem. Soc. 73 (1951) 880-881
51. Mete E., Altundaş R., Seçen H., and Balci M. Turk. J. Chem. 27 (2003) 145-153
52. Adam W., and Balci M. Tetrahedron 36 (1980) 833-858
53. Boyd J.D., Foote D.K., and Imagawa D.K. J. Am. Chem. Soc. 102 (1980) 3641-3642
54. Sütbeyaz Y., Seçen H., and Balci M. J. Org. Chem. 53 (1988) 2312
55. Balci M., and Akbulut N. Tetrahedron 41 (1985) 1315
56. Balci M., and Sütbeyaz Y. Tetrahedron Lett. 24 (1983) 311-314
57. Balci M., and Sütbeyaz Y. Tetrahedron Lett. 24 (1983) 4135-4138
58. Wassermann H.H., and Scheffer J.R. J. Am. Chem. Soc. 89 (1967) 3073-3075
59. Turro N.J., Chow M.G., and Rigaudy J. J. Am. Chem. Soc. 101 (1979) 1300-1302
60. Turro N.J., and Chow M.G.J. J. Am. Chem. Soc. 102 (1980) 1190-1192
61. Aubry J.-M., Pierlot C., Rigaudy J., and Schmidt R. Acc. Chem. Res. 36 (2003) 668-675
62. Wasserman H.H., Wiberg K.B., Larsen D.L., and Parr J. J. Org. Chem. 70 (2005) 105-109
63. Matsumoto M., Yamada M., and Watanabe N. Chem. Commun. (2005) 483-485
64. Nishio T., Nishiyama T., Omote Y., Matsumoto M., Yamada M., and Watanabe N. Chem. Commun. (2005) 483-485
65. Tetrahedron Lett. 27 (1986) 5637-5640