Dichlorocarbene Adducts of Sulfolenes and Their Chlorine Reduction Products: Hydrogen Chloride vs. Sulfur Dioxide Elimination. Thiopyran Dioxides and Thiopyrones

Journal of Organic Chemistry

Volumn 46, Issue 22, 1981, Pages 4502-4510

  Gaoni, Y ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

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EID: 4644228213     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00335a037     Document Type: Article

References (27)

1. Mock, W. L. J. Am. Chem. Soc. 1970,92,6918-26 (correction: J. Am. Chem. Soc. 1973, 95, 3656).
2. Gaoni, Y. Tetrahedron Lett. 1978, 3277-8.
3. Gaoni, Y. Tetrahedron Lett. 1976, 2167-70.
4. Gaoni, Y. Tetrahedron Lett. 1977, 947-50.
5. Gaoni, Y. Tetrahedron Lett. 1977, 4521-4.
6. Woodward, R. B.; Hoffmann, R. “The Conservation of Orbital Symmetry”; Academic Press: New York, 1970; pp 46-7.
7. Turk, S. D.; Cobb, R. L. In “1,4-Cycloaddition Reactions”; Hamer, J.; Ed.; Academic Press: New York, 1961; pp 13-45.
8. Boswell, R. F.; Bass, R. G. J. Org. Chem. 1975, 40, 2419-20.
9. Boatman, S.; Hauser, C. R. “Organic Syntheses”; Wiley: New York, 1973; Collect. Vol. V. pp 767-9.
10. Gaoni, Y. Tetrahedron Lett. 1977, 371-4.
11. Crombie, L.; Harper, S. H.; Thompson, D. J. Chem. Soc. 1951, 2906-15. Crombie, L.; Hemesley, P.; Pattenden, G. J. Chem. Soc. C 1969, 1016-24.
12. Kharchenko, V. G.; Chalaya, S. N.; Konovalova, T. M. Chem. Heterocycl. Compd. 1974,10,1155-70; Chem. Heterocycl. Compd. (Engl. Transl.) 1974,10, 1003-15.
13. Mayer, R.; Broy, W.; Zahradnik, R. Adv. Heterocycl. Chem. 1967, 8, 219-76.
14. Chen, C. H.; Reynolds, G. A. J. Org. Chem. 1979, 44, 3144-7 and preceding papers in the series.
15. Bradamante, S.; Pagani, G. J. Chem. Soc., Perkin Trans. 2 1973, 50-1 and preceding papers in the series.
16. Janssen, M. J. In “Organic Sulfur Chemistry”; Stirling, C. J. M. Ed.; Butterworths: London, 1975; pp 19-42.
17. For a review on ring enlargement via dihalocarbene adducts, see: Barlet, R.; Vo-Quang, Y. Bull. Soc. Chim. Fr. 1969, 3729-60.
18. Greenberg, F. H.; Gaoni, Y. J. Org. Chem. 1978, 43, 4966-8.
19. Gaoni, Y.; Greenberg, F. H. J. Org. Chem. 1981, 46, 74-8.
20. Pauson, P. L.; Proctor, G. R.; Rodger, W. J. J. Chem. Soc. 1965, 3037-40.
21. Beak, P.; McLeister-Monroe, E J. Org. Chem. 1969, 34, 589-96.
22. Tarbell, D. S.; Hoffman, P. J. Am. Chem. Soc. 1954, 76,2451-3.
23. Russel, G. A.; Mikol, J. G. In “Mechanisms of Molecular Migrations”; Thyagarajan, B. S., Ed.; Wiley-Interscience; New York, 1968; Vol. 1, pp 157-207.
24. Molenaar, E.; Strating, J. Reel. Trav. Chim. Pays-Bas 1967, 86, 1047-56.
25. Kienzle, F.; Minder, R. E. Helv. Chim. Acta 1976, 59, 439-52.
26. Gaudemar-Bardone, F.; Gaudemar, M. Synthesis 1979, 463-5.
27. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976,41,1879-80.