Ozonolysis of bis-endo-diacylbicyclo[2.2.1]heptenes in dichloromethane- methanol

Tetrahedron

Volumn 67, Issue 38, 2011, Pages 7236-7243

  Lin, Hui Chang ^a,b   Lin, Chu Chung ^a,c   Wu, Hsien Jen ^a,d  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^b CHINA MEDICAL UNIVERSITY   (Taiwan)

^c TaiGen Biotechnology Co Ltd   (Taiwan)

^d YUANPEI UNIVERSITY   (Taiwan)

Author keywords

Bis endo diacylbicyclo 2.2.1 heptenes; Ozonolysis

Indexed keywords

BIS ENDO DIACETYL 7 OXABICYCLO[2.2.1]HEPTENE; BIS ENDO DIACETYLBICYCLO[2.2.2]OCTENE; BIS ENDO DIACYLBICYCLO[2.2.1]HEPTENE; CYCLOHEPTENE; DICHLOROMETHANE; HYDROPEROXIDE; METHANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; OZONOLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE; X RAY ANALYSIS;

EID: 80051802506     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.055     Document Type: Article

References (42)

1. R. Criegee, and G. Wenner Ann. 564 1949 9
2. R. Criegee Ann. 583 1953 1
3. R. Criegee Angew. Chem., Int. Ed. Engl. 11 1975 745
4. P.S. Bailey Ozonation in Organic Chemistry Vol. 1 1978 Academic New York, NY 1982, Vol. 2
5. W.H. Bunnelle Chem. Rev. 91 1991 335
6. K.J. McCullough, and M. Nojima W. Ando, Organic Peroxides 1992 Wiley New York, NY
7. W. Sander Angew. Chem., Int. Ed. Engl. 29 1990 344
8. S. Fliszar, J. Renard, and D.Z. Simon J. Am. Chem. Soc. 93 1971 6953
9. K. Griesbaum, H.J. Greuning, W. Volpp, and I.C. Jung Chem. Ber. 124 1991 947
10. K. Griesbaum, and G. Zwick Chem. Ber. 119 1986 229
11. K. Griesbaum, G. Zwick, S. Agarwal, H. Keul, B. Pfeffer, and R.W. Murray J. Org. Chem. 50 1985 4194
12. B.J. Wojciechowski, C.Y. Chiang, and R.L. Kuczkowski J. Org. Chem. 55 1990 1120
13. K. Griesbaum, and G. Kiesel Chem. Ber. 122 1989 145
14. Z. Paryzek, J. Martynow, and W. Swoboda J. Chem. Soc., Perkin Trans. 1 1990 1222
15. W.H. Bunnelle, and T.A. Isbell J. Org. Chem. 57 1992 729
16. K. Teshima, S.I. Kawamura, Y. Ushigoe, M. Nojima, and K.J. McCullough J. Org. Chem. 60 1995 4755
17. S.L. Schreiber, R.E. Claus, and J. Reagan Tetrahedron Lett. 23 1982 3867
18. Y.S. Hon, and J.L. Yan Tetrahedron Lett. 34 1993 6591
19. C.C. Lin, and H.J. Wu Tetrahedron Lett. 36 1995 9353
20. H.J. Wu, and C.C. Lin J. Org. Chem. 61 1996 3820
21. H.J. Wu, C.S. Chao, and C.C. Lin J. Org. Chem. 63 1998 7687
22. P.D. Williams, and E. LeGoff J. Org. Chem. 46 1981 4143
23. P.D. Williams, and E. LeGoff Tetrahedron Lett. 26 1985 1367
24. H.J. Wu, and C.C. Lin J. Org. Chem. 60 1995 7558
25. H.C. Lin, and H.J. Wu Tetrahedron 56 2000 341
26. H.J. Wu, J.H. Chern, S.L. Wang, and F.L. Liao J. Chin. Chem. Soc. 45 1998 139
27. H.J. Wu, S.H. Tsai, J.H. Chern, and H.C. Lin J. Org. Chem. 62 1997 6367
28. H.J. Wu, and C.Y. Wu Tetrahedron Lett. 38 1997 2493
29. H.J. Wu, and C.Y. Wu J. Org. Chem. 64 1999 1576
30. H.J. Wu, and J.H. Chern Tetrahedron 53 1997 17653
31. H.J. Wu, and J.H. Chern J. Org. Chem. 62 1997 3208
32. D.J. Pasto, J.A. Duncan, and E.F. Silversmith J. Chem. Educ. 51 1974 277
33. E.F. Silversmith, and F.C. Dunson J. Chem. Educ. 50 1973 568
34. P.S. Bailey, and T.M. Ferrell J. Am. Chem. Soc. 100 1978 899
35. R.P. Lattimer, R.L. Kuczkowski, and C.W. Gillies J. Am. Chem. Soc. 96 1974 348
36. D. Cremer J. Am. Chem. Soc. 103 1981 3619
37. R.L. Kuczkowski A. Padwa, 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York,NY 197 276
38. C.C. Lin, and H.J. Wu J. Chin. Chem. Soc. 42 1995 815
39. C.C. Lin, and H.J. Wu Synthesis 1996 715
40. H.J. Wu, F.J. Huang, and C.C. Lin J. Chem. Soc., Chem. Commun. 1991 770
41. C.C. Lin, F.J. Huang, and H.J. Wu J. Chin. Chem. Soc. 43 1996 177
42. Lai, M. C. Master Thesis, Department of Applied Chemistry, National Chiao Tung University, 1996. When the thioester group was replaced with an ester group, the stereochemistry of the products was not determined by X-ray analysis.