The reduction of nitrobenzenes by triethylsilane using Wilkinson's catalyst

Synthetic Communications

Volumn 26, Issue 5, 1996, Pages 973-980

  Brinkman, Herbert R ^a   Miles, William H ^b   Hilborn, Michael D ^b   Smith, Michael C ^b  

^a Synthesis Development   (United States)

^b LAFAYETTE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION;

EID: 0029937216     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003701     Document Type: Article

References (26)

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3. Mahood, S. A.; Schaffner, P. V. L. Org. Synth. Coll. Vol. 2, 1943, 160; Fox, B. A.; Threlfall, T. L. Org Synth. Coll. Vol. 5, 1973, 346.
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11. For further examples of rhodium catalyzed reductions of nitro groups and related reactions see: Liou, K. F.; Cheng, C. H. J. Org. Chem. 1982, 47, 3018. Mahdavi, F.: Bruton, T. C.; Li, Y. J. Org. Chem. 1993, 58, 744. Gargulak, J. D.; Berry, A. J.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem Soc. 1992, 114, 8933.
12. For further examples of rhodium catalyzed reductions of nitro groups and related reactions see: Liou, K. F.; Cheng, C. H. J. Org. Chem. 1982, 47, 3018. Mahdavi, F.: Bruton, T. C.; Li, Y. J. Org. Chem. 1993, 58, 744. Gargulak, J. D.; Berry, A. J.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem Soc. 1992, 114, 8933.
13. For further examples of rhodium catalyzed reductions of nitro groups and related reactions see: Liou, K. F.; Cheng, C. H. J. Org. Chem. 1982, 47, 3018. Mahdavi, F.: Bruton, T. C.; Li, Y. J. Org. Chem. 1993, 58, 744. Gargulak, J. D.; Berry, A. J.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem Soc. 1992, 114, 8933.
14. 3).
15. Triisopropylsilane was also recovered.
16. 3)- See Brown-Wensley, K. A. Organometallics 1987, 6, 1590.
17. Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390.
18. Nickson, T. E. J Org. Chem 1986, 51, 3903.
19. Nickson (ref 14) reported a "poor yield" of the 2-nitro-m-xylene using the Zinin reaction.
20. For examples of the silylation of amines (a) Bonar-Law, R.P.; Davis, A.P.; Dorgan, B.J. Tetrahedron Lett 1990, 31,6721; (b) Matarasso-Tchiroukhine, E. J. Chem, Soc., Chem, Commun. 1990, 681; Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111, For related examples of the silylation of alcohols (a) Gregg, B.T.; Cutler, A.R. Organometallics 1994, 13, 1039; (b) Doyle, M.P., High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. J. Org. Chem. 1990, 55, 6082; Ojima, I.; Kogure, T.; Nihonyanagi, M.; Kono, H.; Inaba, S.; Nagai, Y. Chem Lett. 1975, 501. 17. Feuer, H. Ed., The Chemistry of the Nitro and Nitroso Groups, Interscience: New York, 1970.
21. For examples of the silylation of amines (a) Bonar-Law, R.P.; Davis, A.P.; Dorgan, B.J. Tetrahedron Lett 1990, 31,6721; (b) Matarasso-Tchiroukhine, E. J. Chem, Soc., Chem, Commun. 1990, 681; Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111, For related examples of the silylation of alcohols (a) Gregg, B.T.; Cutler, A.R. Organometallics 1994, 13, 1039; (b) Doyle, M.P., High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. J. Org. Chem. 1990, 55, 6082; Ojima, I.; Kogure, T.; Nihonyanagi, M.; Kono, H.; Inaba, S.; Nagai, Y. Chem Lett. 1975, 501. 17. Feuer, H. Ed., The Chemistry of the Nitro and Nitroso Groups, Interscience: New York, 1970.
22. For examples of the silylation of amines (a) Bonar-Law, R.P.; Davis, A.P.; Dorgan, B.J. Tetrahedron Lett 1990, 31,6721; (b) Matarasso-Tchiroukhine, E. J. Chem, Soc., Chem, Commun. 1990, 681; Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111, For related examples of the silylation of alcohols (a) Gregg, B.T.; Cutler, A.R. Organometallics 1994, 13, 1039; (b) Doyle, M.P., High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. J. Org. Chem. 1990, 55, 6082; Ojima, I.; Kogure, T.; Nihonyanagi, M.; Kono, H.; Inaba, S.; Nagai, Y. Chem Lett. 1975, 501. 17. Feuer, H. Ed., The Chemistry of the Nitro and Nitroso Groups, Interscience: New York, 1970.
23. For examples of the silylation of amines (a) Bonar-Law, R.P.; Davis, A.P.; Dorgan, B.J. Tetrahedron Lett 1990, 31,6721; (b) Matarasso-Tchiroukhine, E. J. Chem, Soc., Chem, Commun. 1990, 681; Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111, For related examples of the silylation of alcohols (a) Gregg, B.T.; Cutler, A.R. Organometallics 1994, 13, 1039; (b) Doyle, M.P., High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. J. Org. Chem. 1990, 55, 6082; Ojima, I.; Kogure, T.; Nihonyanagi, M.; Kono, H.; Inaba, S.; Nagai, Y. Chem Lett. 1975, 501. 17. Feuer, H. Ed., The Chemistry of the Nitro and Nitroso Groups, Interscience: New York, 1970.
24. For examples of the silylation of amines (a) Bonar-Law, R.P.; Davis, A.P.; Dorgan, B.J. Tetrahedron Lett 1990, 31,6721; (b) Matarasso-Tchiroukhine, E. J. Chem, Soc., Chem, Commun. 1990, 681; Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111, For related examples of the silylation of alcohols (a) Gregg, B.T.; Cutler, A.R. Organometallics 1994, 13, 1039; (b) Doyle, M.P., High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. J. Org. Chem. 1990, 55, 6082; Ojima, I.; Kogure, T.; Nihonyanagi, M.; Kono, H.; Inaba, S.; Nagai, Y. Chem Lett. 1975, 501. 17. Feuer, H. Ed., The Chemistry of the Nitro and Nitroso Groups, Interscience: New York, 1970.
25. For examples of the silylation of amines (a) Bonar-Law, R.P.; Davis, A.P.; Dorgan, B.J. Tetrahedron Lett 1990, 31,6721; (b) Matarasso-Tchiroukhine, E. J. Chem, Soc., Chem, Commun. 1990, 681; Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111, For related examples of the silylation of alcohols (a) Gregg, B.T.; Cutler, A.R. Organometallics 1994, 13, 1039; (b) Doyle, M.P., High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. J. Org. Chem. 1990, 55, 6082; Ojima, I.; Kogure, T.; Nihonyanagi, M.; Kono, H.; Inaba, S.; Nagai, Y. Chem Lett. 1975, 501. 17. Feuer, H. Ed., The Chemistry of the Nitro and Nitroso Groups, Interscience: New York, 1970.
26. For examples of the silylation of amines (a) Bonar-Law, R.P.; Davis, A.P.; Dorgan, B.J. Tetrahedron Lett 1990, 31,6721; (b) Matarasso-Tchiroukhine, E. J. Chem, Soc., Chem, Commun. 1990, 681; Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111, For related examples of the silylation of alcohols (a) Gregg, B.T.; Cutler, A.R. Organometallics 1994, 13, 1039; (b) Doyle, M.P., High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. J. Org. Chem. 1990, 55, 6082; Ojima, I.; Kogure, T.; Nihonyanagi, M.; Kono, H.; Inaba, S.; Nagai, Y. Chem Lett. 1975, 501. 17. Feuer, H. Ed., The Chemistry of the Nitro and Nitroso Groups, Interscience: New York, 1970.