Abstract
A number of modern industrial processes are based on the catalytic carbonylation of organic substrates by carbon monoxide [1–4]. Important chemicals incorporating carbon monoxide, such as oxo alcohols, acetic acid, and acetic anhydride are obtained by this route in thousands of metric tons per year [2]. In contrast, the application of carbon monoxide as a reductant in organic synthesis is confined to relatively few examples. In the last 25 years, the catalytic reductive carbonylation of organic nitro compounds has become a very intense field of research. This is due to the fact that a series of industrially important compounds can be obtained from nitro compounds and carbon monoxide in a single step. Among the most important products that can be obtained by this route, ureas and carbamates are final products and intermediates in the synthesis of fertilisers and pesticides. On the other hand, mono- and diisocyanates are very important intermediates in the manufacture of pesticides, polyurethane foam plastics, synthetic leather, adhesives and coating. Carbonylation reactions of organic nitro compounds have been reviewed before [5–8], but these review are now all out of date.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Falbe, J. (Ed.) New Syntheses with Carbon Monoxide, Spinger Verlag, Berlin (1980).
Parshall, G.W. and Ittel, S.D. Homogeneous Catalysis, Second Edition, John Wiley an Sons, New York (1992).
Wender, I. and Pino, P (Eds.) Organic Synthesis via Metal Carbonyls, Vol. I, Interscienc Publishers, New York (1987); ibidem, Vol II, John Wiley and Sons, New York (1977).
Keim, W. (Ed.) Catalysis in C 1 Chemistry, D. Reidel Publishing Company, Dordrech (1983).
Cenini, S., Pizzotti, M., and Crotti, C. in Aspects of Homogeneous Catalysis, R. Ug (Ed.), D. Reidel Publishing Company, Dordrecht, The Netherlands, 1988.
Manov-Yuvenskii V.I. and Nefedov, B.K. Usp.Khim. 50 (1981) 889. Engl.Transl. i Russ. Chem.Rev. 50 (1981) 470.
Iqbal, A.F.M. CHEMTECFI (1974) 566.
Sheldon, R.A. Chemicals from Synthesis Gas,D. Reidel Publishing Company, Dordrech (1988), p.178 and references therein.
Ozaki, S. Chem.Rev. 72 (1972) 457.
Tsumura, R., Takaki, U., and Takeshi, A. Ger.Offen. 2,635,490 (1977). Chem.Abstr. 87: 23929v.
Fukuoka, S, Chono, M., and Khono, M. CHEMTECH (1984) 670.
Fukuoka, S, Chono, M., and Khono, M J.Org.Chem. 49 (1984) 1458.
Romano, U., Tesei, R., Massi Mauri, M., and Rebora, P. Ind.Eng.Chem.Prod.Res.Dev 19 (1980) 396.
Massi Mauri, M., Romano, U., and Rivetti, F. Ing.Chim.Ital. 21 (1982) 6.
Romano, U., Fornasari, G., and Di Gioacchino, S. Ger.Offen. DE 3,202,690 (1982) Chem.Abstr.: 97:144607d.
Porta, F., Cenini, S. Pizzotti, M., and Crotti, C. Gazz.Chinz.ltal. 115 (1985) 275.
La Monica, G., Monti, C., and Cenini, S. J.Mol.Catal. 18 (1983) 93.
Feuer, H. (Ed.) The Chemistry of the Nitro and Nitroso Groups,Part 1, Interscienc Publishers, New York (1969) and references therein.
Shlyapochnikov, V.A., Khaikin, L.S., Grikina, O.E., Bock, C.W., and Vilkov, L.V J.Mol.Struct. 326 (1994) 1.
Yamamoto T., Kubota, M., Miyashita, A., and Yamamoto, A. Bull.Chem.Soc.Jpn. 5 (1978) 1835.
Izakovich, E.N. and Khidekel’, M.L. Usp.Khim. 57 (1988) 753. Engl.Transl. in Russ.Chem.Rev. 57 (1988) 419.
Cameron, M., Gowenlock, B.G., and Vasapollo, G. Chem.Soc.Rev. 19 (1990) 355.
Grossman, R.F. J.Org.Chem. 22 (1957) 581.
Norbury, A.H. and Sinha, A.I.P. J.Chem.Soc.(A) (1966) 1814.
Hurlburt, P.K., Kellet, P.J., Anderson, O.P., and Strauss, S.H J.Chem.Soc.Chem.Commun. (1990) 576.
Trotter, J. Acta Cryst. 12 (1959) 884.
Sadova, N.I. and Vilkov, L.V. Usp.Kim. 51 (1982) 153. Engl.Transl. in Russ.Chem.Rev 51 (1982) 87.
Lanfranchi, M., Pellinghelli, M.A., Predieri, G., Bigi, F., Maggi, R., and Sartori, G J.Chem.Soc., Dalton Trans. (1993) 1463.
Izakovich, E.N., Kachapina, L.M., Shibaeva, R.P., and Khidekel’, M.L. 4 11 ’ haernationa Symposium on Homogeneous Catalysis (ISHC4),Leningrad (1984) Book IV, P9–29, p.65.
Vicente, J., Martin, J., Chicote, M.-T., Solans, X., and Miravitlles, C J.Chem.Soc., ChencCommun. (1985) 1004.
Vicente, J., Martin, J., Solans, X., and Font-Altaba, M. Organometallics 8 (1989) 357.
Vicente, J., Chicote, M.-T., Martin, J., Jones, P.G., Fittschen, C., and Sheldrich, G.M J.Chem.Soc., Dalton Trans. (1986) 2215.
Vicente, J., Chicote, M.-T., Martin, J., Jones, P.G., and Fittschen, C. J.Chem.Soc., Dalto Trans. (1987) 881.
Vicente, J., Chicote, M.-T., Martin, J., Artigao, M., Solans, X., Font-Altaba, M., an Aguilb, M. J.Chem.Soc., Dalton Trans. (1988) 141.
Vicente, J., Abad, J.A., Lahoz, F.J., and Plou, F.J. J.Chem.Soc., Dalton Trans. ( 1990 1459.
Clark, G.R., Headford, C.E.L., Roper, W.R., Wright, L.J., and Yap, P.D. Inorg,Chim.Act 220 (1994) 261.
Naldini, L., Panzanelli, A., Rassu, G., Cariati, F., Demartin, F., Manassero, M., an Masciocchi, N. Inorg, Chim.Aeta 83 (1984) L71.
Adrianov, V.G., Struchkov, Yu.T., Pyslmograeva, N.I., Setkina, V.N., and Kursanov, D. N J.Organomet.Chem. 206 (1981) 177.
Crabtree, RH., Davis, M.W., Mellea, M.F., and Mihelcic, J.M. Inorg.Chim.Acta 7 (1983) 223.
Unverferth, K., Höntsch, R., and Schwetlick, K. J.Prakt.Chenr. 321 (1979) 86 Chem.Abstr.: 91: 19355v.
Unverferth, K., Höntsch, R., and Schwetlick, K. J.Prakt.Chem. 321 (1979) 928 Chem.Abstr.: 93: 25645x.
Alberti, A. and Camaggi, C.M. J.Organomet.Chenr. 194 (1980) 343.
Sherlock, S.J., Boyd, D.C., Moasser, B., and Gladfelter, W.L. Inorg.Chem. 30 ( 1991 3626.
Skoog, S.J., Campbell, J.P., and Gladfelter, W.L. Organometallics 13 (1994) 4137.
Ragaini, F., Cenini, S., and Demartin, F. Organometallics 13 (1994) 1178.
Liu, P.-H., Liao, H.-Y., and Cheng, C.-H. J.Chem.Soc., Chem.Commun. (1995) 2441.
Bellon, P.L., Cenini, S., Demartin, F., Pizzotti, M., and Porta, F J.Chem.Soc.,Chem.Commun. (1982)265.
Cenini, S., Porta, F., Pizzotti, M., and Crotti, C. J.Chem.Soc., Dalton Trans. (1985) 163.
Berman, R.S. and Kochi, J.K. Inorg.Chem. 19 (1980) 248.
Koerner von Gustorf, E. Angew.Chem.Int.Ed.Engl. 5 (1966) 739.
Koerner von Gustorf, E. and Jun, M.-J. Zeit.Naturforsh. 20b (1965) 521.
Barrows, M.J. and Mills, O.S. J.Chem.Soc.(A) (1971) 864.
Pizzotti, M., Crotti, C., and Demartin, F. J.Chem.Soc., Dalton Trans. (1984) 735.
Dekker, M. and Knox, G.R. J.Chem.Soc.,Chem.Commun. (1967) 1243.
Wade, K. Adv.Inorg.Chenr.Radiochem. 18 (1976) 1.
Alper, H. Inorg.Chem. 11 (1972) 976.
Aime, S., Gervasio, G., Milone, L., Rossetti, R., and Stanghellini, P.L J.Chem.Soc., Dalton Trans. (1978) 534.
Gervasio, G., Rossetti, R., and Stanghellini, P.L. J.Chem.Soc., Chem. Commun. ( 1977 387.
Landesberg, J.M., Katz, L., and Olsen, C. J.Org.Chern. 37 (1972) 930.
Alper, H. and Paik, H.-N. Nouv.J.Chim. 2 (1977) 245.
Sappa, E., and Milone, L. JOrganomet.Chem. 61 (1973) 383.
Bhaduri, S., Gopalkrishnan, K.S., Sheldrick, G.M., Clegg, W., and Stalke, D J.Chem.Soc., Dalton Trans. (1983) 2339.
Morrison, D.L. and Wigley, D. E. J.Chem.Soc.Chem.Conmmn. (1995) 79.
Andrews, M.A. and Kaesz, H.D. J.Am.Chem.Soc. 101 (1979) 7255.
Ragaini, F., Song, J.-S., Ramage, D.L., Geoffroy, G.L., Yap, G.A.P., and Rheingold, A.L Organometallics 14 (1995) 387.
Ragaini, F. Organometallics in press.
Bhaduri, S., Gopalkrishnan, K.S., Clegg, W., Jones, P.G., Sheldrick, G.M., and Stalke, D J.Chem.Soc., Dalton Trans. (1984) 1765.
Floriani, C. and Fachinetti, G. J.Chem.Soc., Chem.Commun. (1973) 17.
Maatta, E.A. and Wentworth, R.A.D. Inorg.Chem. 19 (1980) 2597.
Alper, H., Petrignani, J.-F., Einstein, F.W.B., and Willis, A.C. J.Am.Chem.Soc. 10 (1983) 1701.
Petrignani, J.-F. and Alper, H. Inorg.Chinr.Acta 77 (1983) L243.
Fletcher, J., Hogarth, G., and Tocher, D.A. J.Organomet.Chem. 403 (1991) 345.
Fawcett, J., Holloway, J.H., Hope, E.G., Russel, D.R., Saunders, G.C., and Atherton, M. J J.Organomet.Chern. 464 (1994) C20.
Ragaini, F. and Cenini, S. Unpublished results.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1997 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Cenini, S., Ragaini, F. (1997). Introduction. In: Catalytic Reductive Carbonylation of Organic Nitro Compounds. Catalysis by Metal Complexes, vol 20. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-0986-6_1
Download citation
DOI: https://doi.org/10.1007/978-94-017-0986-6_1
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-4766-3
Online ISBN: 978-94-017-0986-6
eBook Packages: Springer Book Archive