Aromatic thioesters as protecting groups for thiols against 1,2-didehydrobenzenes

European Journal of Organic Chemistry

Volumn , Issue 6, 2007, Pages 1013-1017

  Fowelin, Christian ^a   Schüpbach, Björn ^a   Terfort, Andreas ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Benzyne; Cycloaddition; Didehydrobenzene; Protecting groups; Thiols; Triptycenes

Indexed keywords

EID: 34250657457     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600713     Document Type: Article

References (38)

1. A whole issue of Acc. Chem. Res. was recently dedicated to this topic: Acc. Chem. Res. 2001, 34, Issue 6.
2. K. Kinbara, T. Aida, Chem. Rev. 2005, 105, 1377.
3. T. R. Kelly, H. De Silva, R. A. Silva, Nature 1999, 401, 150.
4. T. R. Kelly, J. P. Sestelo, I. Tellitu, J. Org. Chem. 1998, 63, 3655.
5. D. C. Caskey, B. Wang, X. Zheng, J. Michl, Collect. Czech. Chem. Commun. 2005, 70, 1970.
6. J. C. Bryan, R. A. Sachleben, A. A. Gakh, G. J. Bunick, J. Chem. Crystallogr. 1999, 29, 513.
7. R. A. van Delden, M. K. J. ter Wiel, M. M. Pollard, J. Vicario, N. Koumura, B. L. Feringa, Nature 2005, 437, 1337.
8. X. Marguerettaz, G. Redmond, S. N. Rao, D. Fitzmaurice, Chem. Eur. J. 1996, 2, 420.
9. P. Laitenberger, C. G. Claessens, F. M. Kuipers, F. M. Raymo, R. E. Palmer, J. F. Stoddart, Chem. Phys. Lett. 1997, 279, 209.
10. T. R. Kelly, Acc. Chem. Res. 2001, 34, 514.
11. V. R. Skvarchenko, V. K. Shalaev, E. I. Russ. Klabunovskii, Chem. Rev. 1974, 74, 951.
12. Q.-S. Zong, C.-F. Chen, Org. Lett. 2006, 8, 211.
13. K. Gong, X. Zhu, R. Zhao, S. Xiong, L. Mao, C. Chen, Anal. Chem. 2005, 77, 8158.
14. X.-Z. Zhu, C.-F. Chen, J. Am. Chem. Soc. 2005, 127, 13158.
15. R. W. Hoffmann, Chem. Acetylenes 1969, 1063.
16. S. Gilchrist in The Chemistry of Functional Groups, Suppl. C (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1983.
17. S. V. Kessar, Acc. Chem. Res. 1978, 7, 283.
18. M. Simmonds in Rodd's Chemistry of Carbon Compounds, 2nd ed. (Ed.: M. Sainsbury), Elsevier, Amsterdam, 1996.
19. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York, 1967.
20. E. C. Kornfeld, P. Barney, J. Blankley, W. Faul, J. Med. Chem. 1965, 8, 342.
21. J. Nakayama, K. Akimoto, Sulfur Reports 1994, 16, 61.
22. N. Nakamura, Chem. Lett. 1983, 12, 1795.
23. F. M. Callahan, G. W. Anderson, R. Paul, J. E. Zimmerman, J. Am. Chem. Soc. 1963, 85, 201.
24. O. Nishimura, C. Kitada, M. Fujino, Chem. Pharm. Bull. 1978, 26, 1576.
25. S. Sakakibara, Y. Shimonishi, Y. Kishida, M. Okada, H. Sugihara, Bull. Chem. Soc. Jpn. 1967, 40, 2164.
26. B. Zeysing, C. Gosch, A. Terfort, Org. Lett. 2000, 2, 1843.
27. G. Wittig, E. Benz, Chem. Ber. 1958, 91, 873.
28. F. M. Beringer, S. J. Huang, J. Org. Chem. 1964, 29, 445.
29. L. Friedman, F. M. Logullo, J. Am. Chem. Soc. 1963, 85, 1549.
30. L. Friedman, F. M. Logullo, J. Org. Chem. 1969, 34, 3089.
31. Y. Mimeshima, T. Sonoda, H. Kobayashi, Chem. Lett. 1983, 1211.
32. T. Abe, T. Yamaji, T. Kitamura, Bull. Chem. Soc. Jpn. 2003, 76, 2175.
33. E. Ciganek, J. Org. Chem. 1980, 45, 1497.
34. In the case of the electron-poor aromatic thioesters, we expected the formation of intramolecular CT complexes. We were able to obtain crystals of 2g suitable for X-ray-diffraction analysis. These results are presented in the Supporting Information.
35. The syntheses of these compounds are described in the Supporting Information.
36. B. H. Klanderman, T. R. Criswell, J. Org. Chem. 1969, 34, 3426.
37. CCDC-273363 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
38. H. J. Lorkowski, R. Pannier, A. Wende, J. Prakt. Chem. 1967, 35, 149.