Oxidation of some alkoxy-cycloheptatriene derivatives: unusual formation of furan and furanoids from cycloheptatrienes

Tetrahedron

Volumn 63, Issue 23, 2007, Pages 4944-4950

  Coşkun, Ahmet ^a,b   Güney, Murat ^b   Daştan, Arif ^b   Balci, Metin ^c  

^a SELCUK UNIVERSITY   (Turkey)

^b ATATÜRK UNIVERSITY   (Turkey)

^c MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Cycloheptatriene; Endoperoxide; Furan derivatives; Rearrangement; Singlet oxygen; Tropolone; Tropone

Indexed keywords

3 CHLOROPERBENZOIC ACID; ALKOXY CYCLOHEPTATRIENE DERIVATIVE; FURAN; FURANOID DERIVATIVES; TROPONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MASS SPECTROMETRY; OXIDATION; PRIORITY JOURNAL;

EID: 34247642191     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.145     Document Type: Article

References (36)

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. Scott A.I., and Lee E. J. Chem. Soc., Chem. Commun. (1972) 655-656
6. Scott A.I., and Weisner K.J. J. Chem. Soc., Chem. Commun. (1972) 1075-1077
7. Scott A.I., Guilford H., and Lee E. J. Am. Chem. Soc. 93 (1971) 3534-3536
8. Johns R.B., Johnson A.W., and Murray J. J. Chem. Soc. (1954) 2352-2356
9. Bartels-Keith J.R., Johnson A.W., and Taylor W.I. J. Chem. Soc. (1951) 198-202
10. Asao T., Yahigara M., and Kitahara Y. Bull. Chem. Soc. Jpn. 51 (1978) 2131-2135
11. Oda M., and Kitahara M. Tetrahedron Lett. (1969) 3295-3296
12. Daştan A., Yi{dotless}ldi{dotless}z Y.K., Kazaz C., and Balci M. Turk. J. Chem. 26 (2002) 143-151
13. Daştan A., Yi{dotless}ldi{dotless}z Y.K., and Balci M. Synth. Commun. 31 (2001) 3807-3815
14. Shono T., Nozoe T., Maekava H., and Kashimura S. Tetrahedron Lett. 29 (1988) 555-558
15. Ikeda Y., Mori A., and Takeshita H. Bull. Chem. Soc. Jpn. 66 (1993) 2779-2780
16. Takeshita H., Mori A., and Suizi H. Bull. Chem. Soc. Jpn. 60 (1987) 1429-1432
17. Güney M., Çelik Z.C., Daştan A., and Balci M. Can. J. Chem. 83 (2005) 227-235
18. Balci M. Chem. Rev. 81 (1981) 91-108
19. Dastan A., Saracoglu N., and Balci M. Eur. J. Org. Chem. (2001) 3519-3522
20. Dastan A., and Balci M. Tetrahedron 62 (2006) 4003-4010
21. Güney M., Daştan A., and Balci M. Helv. Chim. Acta 88 (2005) 830-838
22. In: Wassermann H.H., and Murray R.W. (Eds). Singlet Oxygen. Organic Chemistry, A Series of Monograph Vol. 40 (1979), Academic, New York, NY
23. Fukunaga T., and Simmons H.E. J. Am. Chem. Soc. 89 (1967) 5208-5215
24. Rieche A., Schmitz E., and Beyer E. Chem. Ber. 91 (1958) 1935-1941
25. Wiseman R.L., Johnson S.M., Kelker M.S., Foss T., Wilson I.A., and Kelly J.W. J. Am. Chem. Soc. 127 (2005) 5540-5551
26. Wu Z., Stanley R.R., and Pittman Jr. C.U. J. Org. Chem. 64 (1999) 8386-8395
27. Mori A., and Takeshita H. Kyushu Daigaku Sogo Rikogaku Kenkyuka Hokoku 3 (1981) 125-130
28. Boyd J.D., Foote C.S., and Imagawa D.K. J. Am. Chem. Soc. 102 (1980) 3641-3642
29. Sütbeyaz Y., Seçen H., and Balci M. J. Org. Chem. 53 (1988) 2312-2317
30. Balci M., and Akbulut N. Tetrahedron 41 (1985) 1315-1322
31. Balci M., and Sütbeyaz Y. Tetrahedron Lett. 24 (1983) 311-314
32. Balci M., and Sütbeyaz Y. Tetrahedron Lett. 24 (1983) 4135-4138
33. Sanchez V., Rebolledo F., and Gotor V. Synlett (1994) 529-530
34. For alternate synthesis of the diacetate, see:. Takeshita H., Mori A., Kusaba T., and Watanabe H. Bull. Chem. Soc. Jpn. 60 (1987) 4325-4333
35. Secen H., Sutbeyaz Y., Salamci E., and Balci M. Turk. J. Chem. 16 (1992) 237-245
36. Kusaba T., Mori A., and Takeshita H. Bull. Chem. Soc. Jpn. 58 (1985) 515-520