Reductive elimination of phenylsulfonyl groups in the 3-position of benzo[a]heptalene-2,4-diols

Helvetica Chimica Acta

Volumn 88, Issue 5, 2005, Pages 1085-1101

  Fattah, Mohy Eldin Abdel ^a   El Rayes, Samir ^a   Soliman, El Sayed Ahmed ^b   Linden, Anthony ^c   Abou Hadeed, Khaled ^c   Hansen, Hans Jürgen ^c  

^a Suez Canal University   (Egypt)

^b Ain Shams University   (Egypt)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; BOILING LIQUIDS; CHEMICAL ANALYSIS; COMPLEXATION; LITHIUM COMPOUNDS; REDUCTION;

CLEAVAGE; DESULFONYLATION; PHENYLSULFONYL GROUPS;

SULFUR COMPOUNDS;

2,4 DIHYDROXYBENZO[A]HEPTALENE 3 THIOL; 3 (PHENYLSULFONYL)BENZO[A]HEPTALENE 2,4 DIOL; 3,3' DITHIOBIS(9 ISOPROPYL 7,12 DIMETHYLBENZO[A]HEPTALENE 2,4 DIOL; 9 ISOPROPYL 2,4 DIMETHOXY 7,12 DIMETHYL 3 (PHENYLSULFONYL)BENZO[A]HEPTALENE; BENZENE DERIVATIVE; BENZENESULFONIC ACID DERIVATIVE; BENZO[A]HEPTALENE 2,4 DIOL; DISULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

EID: 20344363162     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590080     Document Type: Article

References (42)

1. K. Abou-Hadeed, H.-J. Hansen, Helv. Chim. Acta 1997, 80, 2535.
2. M. Lutz, A. Linden, K. Abou-Hadeed, H.-J. Hansen, Helv. Chim. Acta 1999, 82, 372.
3. M. Meyer, K. Abou-Hadeed, H.-J. Hansen, Helv. Chim. Acta 2000, 83, 2383.
4. K. Abou-Hadeed, H.-J. Hansen, Helv. Chim. Acta 2003, 86, 4018.
5. a) S. El Rayes, K. Abou-Hadeed, H.-J. Hansen, Autumn Meeting of the Swiss Chemical Society, Zurich, 2001; Poster No. 139 (cf. Chimia 2001, 55, 621);
6. b) K. Abou-Hadeed, H.-J. Hansen, Autumn Meeting of the Swiss Chemical Society, Zurich, 2001; Poster No. 218.
7. I. G. Anderson, M. P. Balfe, J. Kenyon, J. Chem. Soc. 1951, 385.
8. R. E. Dabby, J. Kenyon, R. F. Mason, J. Chem. Soc. 1952, 4881.
9. L. Hornet, R.-E. Schmitt, Acta Chem. Scand. B 1983, 37, 469.
10. W. E. Truce, D. P. Tate, D. N. Burdge, J. Am. Chem. Soc. 1960, 82, 2872.
11. L. Horner, E. Meyer, Liebigs Ann. Chem. 1975, 2053.
12. L. Horner, E. Meyer, Ber. Bunsenges. 1975, 79, 143.
13. A. Bortel, E. Fouret, O. Fourets, J.-F. Pilard, New J. Chem. 2000, 24, 815.
14. H. Lund, in Organic Electrochemistry', 4th edn., Eds. H. Lund, O. Hemmerich, Marcel Dekker, New York, 2001, p. 964.
15. R. Mozingo, D. E. Wolf, S. A. Harris, K. Folkers, J. Am. Chem. Soc. 1943, 65, 1013.
16. H. C. Brown, S.-C. Kim, S. Krishnamurthy, Organometallics 1983, 2, 779.
17. W. G. Brown, Org. React. 1951, 6, 469.
18. a) F. C. Bordwell, W. H. McKellin, J. Am. Chem. Soc. 1951, 73, 2251;
19. b) T. A. Whitney, D. J. Cram, J. Org. Chem. 1970, 35, 3964;
20. W. P. Weber, P. Stromquist, T. S. Ito, Tetrahedron Lett. 1974, 30, 2595.
21. D. Klamann, Monatsh. Chem. 1953, 84, 651.
22. J. N. Gardner, S. Kaiser, A. Krubiner, H. Lucas, Can. J. Chem. 1973, 51, 1419.
23. E. Akgün, K. Mahmood, C. A. Mathis, J. Chem. Soc., Chem. Commun. 1994, 761.
24. P. Uebelhart, C. Weymuth, A. Linden, H.-J. Hansen, Helv. Chim. Acta 2005, 88, in preparation.
25. J. Drabowicz, M. Mikolajczyk, Synthesis 1976, 527.
26. M. A. Francisco, A. Kurs, A. R. Katritzky, D. Rasala, J. Org. Chem. 1988, 53 596.
27. R. Gerdil, E. A. C. Ludie;cken, J. Chem. Soc. 1963, 5444.
28. C. Cheng, L. M. Stock, J. Org. Chem. 1991, 56, 2436.
29. 'CRC Handbook of Chemistry and Physics', 70th edn., CRC Press, Boca Raton, FL, 1989-1990, p. D-158 and D-160.
30. D. Wittenberg, T. C. Wu, H. Oilman, J. Org. Chem. 1958, 23, 1898.
31. N. Furukawa, H. Tanaka, S. Oae, Bull. Chem. Soc. Jpn. 1968, 41, 1463.
32. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
33. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, Macromolecular Crystallography, Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, London, 1997, p. 307.
34. R. S. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33.
35. G. M. Sheldrick, SHELXS97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997.
36. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
37. E. N. Maslen, A. G Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, p. 477.
38. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
39. D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.4.3, p. 200.
40. G. M. Sheldrick, 'SHELXS97', Program for the Refinement of Crystal Structures, 1997.
41. teXsan, Single Crystal Structure Analysis Software, Version 1.10, Molecular Structure Corp., The Woodlands, Texas, 1999.
42. C. K. Johnson, ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.