Preparation of chiral hydroxy carbonyl compounds and diols by ozonolysis of olefinic isoborneol and fenchol derivatives: Characterization of stable ozonides by 1H-, 13C-, and 17O-NMR and electrospray ionization mass spectrometry

Helvetica Chimica Acta

Volumn 82, Issue 9, 1999, Pages 1385-1399

  Kostova, Kalina ^a   Dimitrov, Vladimir ^a   Simova, Svetlana ^a   Hesse, Manfred ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY SPECTROMETRY;

EID: 0032877529     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19990908)82:9<1385::AID-HLCA1385>3.0.CO;2-Y     Document Type: Article

References (34)

1. D. G. Lee, T. Chen, in 'Comprehensive Organic Chemistry', Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, Vol. 7, p. 541.
2. J. F. Callahan, K. A. Newlander, H. G. Bryan, W. F. Huffman, M. L. Moore, N. C. F. Yim, J. Org. Chem. 1988, 53, 1527.
3. R. A. Bartsch, B. R. Cho, M. J. Pugia, J. Org. Chem. 1987, 52, 5492.
4. G. N. Walker, J. Am. Chem. Soc. 1957, 79, 3508.
5. C. R. Bertozzi, M. D. Bednarski, Tetrahedron Lett. 1992, 33, 3109; M. Isobe, H. Iio, T. Kawai, T. Goto, ibid. 1977, 8, 703.
6. C. R. Bertozzi, M. D. Bednarski, Tetrahedron Lett. 1992, 33, 3109; M. Isobe, H. Iio, T. Kawai, T. Goto, ibid. 1977, 8, 703.
7. a) Y.-S. Hon, L. Lu, S.-Y. Li, J. Chem. Soc., Chem. Commun. 1990, 1627;
8. b) Y.-S. Hon, K.-P. Chu, P.-C. Hong, L. Lu, Synth. Commun. 1992, 22, 429;
9. c) Y.-S. Hon, S.-W. Lin, Y.-J. Cen, ibid. 1993, 23, 1543;
10. d) Y.-S. Hon, L. Lu, Tetrahedron Lett. 1993, 34, 5309;
11. e) Y.-S. Hon, Y.-L. Yan, ibid. 1993, 34, 6591;
12. f) Y.-S. Hon, J.-L. Yan, ibid. 1994, 35, 1743;
13. g) Y.-S. Hon, F.-J. Chang, L. Lu, J. Chem. Soc., Chem. Commun. 1994, 2041;
14. h) Y-S. Hon, L. Lu, Tetrahedron 1995, 51, 7937.
15. R. Criegee, Angew. Chem. 1975, 87, 765.
16. a) H. Mimoun, Angew. Chem. 1982, 94, 750;
17. b) R. L. Kuczkowski, Acc. Chem. Res. 1983, 16, 42.
18. B. J. Wojciechowski, C.-Y. Chiang, R. L. Kuczkowski, J. Org. Chem. 1990, 55, 1120.
19. A. Rieche, R. Meister, H. Sauthoff, Liebigs Ann. Chem. 1942, 553, 246.
20. a) J. Lauterwein, K. Griesbaum, P. Krieger-Beck, V. Ball, K. Schlindwein. J. Chem. Soc., Chem. Commun. 1991, 816;
21. b) K. Griesbaum, K. Schlindwein, M. Hilss, Chem. Ber. 1993, 126, 1843;
22. c) F. Hock, V. Ball, Y. Dong, S.-H. Gutsche, M. Hilss, K. Schlindwein, K. Griesbaum, J. Magn. Res. Ser. A 1994, 111, 150.
23. V. Dimitrov, S. Bratovanov, S. Simova, K. Kostova, Tetrahedron Lett. 1994, 35, 6713; V. Dimitrov, S. Simova, K. Kostova, Tetrahedron 1996, 52, 1699.
24. V. Dimitrov, S. Bratovanov, S. Simova, K. Kostova, Tetrahedron Lett. 1994, 35, 6713; V. Dimitrov, S. Simova, K. Kostova, Tetrahedron 1996, 52, 1699.
25. V. Dimitrov, K. Kostova, M. Hesse, Tetrahedron: Asymmetry 1994, 5, 1891.
26. a) V. Dimitrov, M. Genov, S. Simova, A. Linden, J. Organomet. Chem. 1996, 525, 213;
27. b) V. Dimitrov, K. Kostova, M. Genov, Tetrahedron Lett. 1996, 37, 6887;
28. c) V. Dimitrov, I. Philipova, S. Simova, Tetrahedron: Asymmetry 1996, 7, 1493;
29. d) M. Genov, K. Kostova, V. Dimitrov, ibid. 1997, 8, 1869.
30. D. Gupta, R. Soman, S. Dev, Tetrahedron 1982, 38, 3013.
31. M. Pirrot, M. El Idrissi, M. Santelli, Tetrahedron Lett. 1989, 30, 461.
32. Y. Ushigoe, S. Tanaka, M. Nojima, K. J. McCullough, Tetrahedron Lett. 1994, 35, 9741, K. Teshima, S. Kawamura, Y. Ushigoe, M. Nojima, K. J. McCullough, J. Org. Chem. 1995, 60, 4755.
33. Y. Ushigoe, S. Tanaka, M. Nojima, K. J. McCullough, Tetrahedron Lett. 1994, 35, 9741, K. Teshima, S. Kawamura, Y. Ushigoe, M. Nojima, K. J. McCullough, J. Org. Chem. 1995, 60, 4755.
34. 129Xe-NMR-Spektroskopie', Georg Thieme Verlag, New York, 1992.