Cyclization of Aryl Silanes with Unexpected Retention of Silicon

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3797-3798

  Fearnley, Stephen Philip ^a   Tidwell, Michael W ^a  

^a LAMAR UNIVERSITY   (United States)

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ARTICLE;

EID: 0041673767     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026494h     Document Type: Article

References (34)

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15. Other related studies: (d) Martin, O. R.; Rao, S. P.; El-Shenawy, H. A.; Kurz, K. G.; Cutler, A. B. J. Org. Chem. 1988, 53, 3287. (e) Martin, O. R.; Rao, S. P.; Kurz, K. G.; El-Shenawy, H. A. J. Am. Chem. Soc. 1988, 110, 8698.
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17. For example, double C-glycosidation: Martin, O. R.; Mahnken, R. E. J. Chem. Soc., Chem. Commun. 1986, 497. Martin, O. R.; Rao, S. P.; Hendricks, C. A. V.; Mahnken, R. E. Carbohydr. Res. 1990, 202, 49.
18. A brief survey of unactivated benzyl substrates is illustrative. 1,6-Anhydro-D-glucose: no tricyclic products (ref 3b). 1-O-Acetyl hexapyranoses (manno- and gluco-): "complex mixtures" (refs 2a and 3a). α-Glucopyranosyl chloride: 74% yield. Verlhac, P.; Leteux, C.; Toupet, L.; Veyrières, A. Carbohydr. Res. 1996, 291, 11.
19. For reviews of arylsilanes in regiospecific electrophilic aromatic substitutions, see: Eaborn, C. J. Organomet. Chem. 1975, 100, 43, Fleming, I. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 3, Chapter 13, p 613.
20. For reviews of arylsilanes in regiospecific electrophilic aromatic substitutions, see: Eaborn, C. J. Organomet. Chem. 1975, 100, 43, Fleming, I. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 3, Chapter 13, p 613.
21. For specific intramolecular examples, see: (a) Miller, R. B.; Tsang, T. Tetrahedron Lett. 1988, 29, 6715. (b) Majetich, G.; Zhang, Y.; Feltmann, T. L.; Belfoure, V. Tetrahedron Lett. 1993, 34, 441. (c) Cho, I.-S.; Tu, C.-L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 3594.
22. For specific intramolecular examples, see: (a) Miller, R. B.; Tsang, T. Tetrahedron Lett. 1988, 29, 6715. (b) Majetich, G.; Zhang, Y.; Feltmann, T. L.; Belfoure, V. Tetrahedron Lett. 1993, 34, 441. (c) Cho, I.-S.; Tu, C.-L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 3594.
23. For specific intramolecular examples, see: (a) Miller, R. B.; Tsang, T. Tetrahedron Lett. 1988, 29, 6715. (b) Majetich, G.; Zhang, Y.; Feltmann, T. L.; Belfoure, V. Tetrahedron Lett. 1993, 34, 441. (c) Cho, I.-S.; Tu, C.-L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 3594.
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26. Overall yield was highly susceptible to concentration, e.g., at reflux: 0.276 M, 19%; 0.036 M, 45%; 0.004 M. 72%.
27. Dupré, B.; Meyers, A. I. J. Org. Chem. 1991, 56, 3197.
28. Prepared from the known phenol: Speier, J. L. J. Am. Chem. Soc. 1952, 74, 1003. See Supporting Information for details.
29. This also discounted a 1,5-silylatropic shift in the intermediate cation and electrophilic aromatic substitutions by opportunistic TMS-X species.
30. For example, see: Ishibashi, H.; Sakashita, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1992, 1953 and references therein.
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32. PC Spartan Pro, AM1 parametrization.
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34. Mills, W. H.; Nixon, I. G. J. Chem. Soc. 1930, 2510. For a discussion correctly refuting this phenomenon, see: Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1721.