Thermal rearrangement of 1,3-thiazolidine sulfoxides: Thiolsulfinate and thioaldehyde intermediates

Journal of Heterocyclic Chemistry

Volumn 36, Issue 1, 1999, Pages 271-276

  Hahn, Hoh Gyu ^a   Nam, Kee Dal ^c   Mah, Heduck ^b  

^a Korea Institute of Science and Technology   (South Korea)

^b Kyunggi University   (South Korea)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE; THIAZOLIDINE DERIVATIVE; THIOALDEHYDE;

ARTICLE; CYCLIZATION; HEATING; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 13044317279     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360141     Document Type: Article

References (28)

1. [a] W. S. Lee, H. G. Hahn and K. D. Nam, J. Org. Chem., 51, 2789 (1986);
2. [b] H. D. Mah and W. S. Lee, J. Heterocyclic Chem., 26, 1447 (1989);
3. [c] W. S. Lee, K. Lee, K. D. Nam and Y. J. Kim, Tetrahedron, 47, 8091 (1991);
4. [d] W. S. Lee, K. D. Nam and H. G. Hahn, J. Heterocyclic Chem., 30, 1105 (1993).
5. [a] H. G. Hahn and W. S. Lee, J. Chem. Res. (S), 86 (1995); J. Chem. Res. (m), 0630 (1995);
6. [a] H. G. Hahn and W. S. Lee, J. Chem. Res. (S), 86 (1995); J. Chem. Res. (m), 0630 (1995);
7. [b]. H. Mah, K. D. Nam and H. G. Hahn, Heterocycles, 45, 1999 (1997).
8. E. Block, J. Am. Chem. Soc., 94, 642, 644 (1972).
9. H. J. Reich, F. Chew and S. L. Peake, Synthesis, 299 (1978).
10. 1H nmr spectroscopy.
11. [a] D. N. Jones, D. R. Hill, D. A. Lewton and C. Sheppard, J. Chem. Soc. Perkin Trans., 1, 1574 (1977);
12. [b] D. N. Jones, D. R. Hill and D. A. Lewton, Tetrahedron Letters, 27, 2235 (1975).
13. [a] D. R. Hogg, Comprehensive Organic Chemistry, Pergamon Press, Oxford, 1979, 3, pp262-267;
14. [b] F. A. Davis and R. L. Billmers, J. Am. Chem. Soc., 103, 7016 (1981);
15. [c] E. Block and J. O'Connor, ibid 96, 3929 (1974).
16. Although tlc clearly revealed the presence of 17, it was too scarce to isolate it by chromatography. We prepared 17 by an independent synthesis [2b].
17. S. Oae, Organic Sulfur Chemistry: Structure and Mechanism, CRCPress, London, 1991, pp 134-135.
18. Sulfinic acid is known to be thermally unstable and undergo acid-catalyzed, dehydrative disproportionation to yield thiosulfonate and sulfonic acid [11]. However, we could not isolate either 34 or 35. (Chemical Equation Presented)
19. S. Oae, Organic Sulfur Chemistry: Structure and Mechanism, CRC Press, London, 1991, p 304.
20. A. Ishii, T. Ishida, N. Kumon, N. Fukuda, N. Oyama, N. Inamoto, F. Iwasak and R. Okazaki, Bull. Chem. Soc. Japan, 69, 709 (1996).
21. [a] D. R. Dice and R. P. Steer, Can. J. Chem., 52, 3518 (1974);
22. [b] A. G. Anastassiou, J. C. Wetzel and B. Chao, J. Am. Chem. Soc., 98, 6405 (1976);
23. [c] E. Vedejs, M. J. Arnost, J. M. Dolphin and J. Eustache, J. Org. Chem., 45, 2601 (1980);
24. [d] E. Vedejs, T. H. Eberlein and D. L. Varie, J. Am. Chem. Soc., 104, 1445 (1982);
25. [e] J. E. Baldwin and R. C. G. Lopez, J. Chem. Soc., Chem. Commun., 1029 (1982); J. E. Baldwin and R. C. G. Lopez, Tetrahedron, 39, 1487 (1983).
26. [e] J. E. Baldwin and R. C. G. Lopez, J. Chem. Soc., Chem. Commun., 1029 (1982); J. E. Baldwin and R. C. G. Lopez, Tetrahedron, 39, 1487 (1983).
27. Black precipitates were observed by the treatment of cupric chloride dissolved in 1N hydrochloric acid with the stream of vapor of the reaction mixture during the reaction.
28. H. Shinohara, S. Misaki and E. Imoto, Nippon Kagaku Zasshi, 83, 637 (1962).