Abstract
Carbon monoxide reacts with unsaturated compounds, such as olefins and acetylenes, in the presence of a variety of protic co-substrates and transition metal carbonyl catalysts to afford carboxylic acid derivatives (Reactions 1–6). These transformations are generally referred to as Reppe carbonylations after their discoverer [1].
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
W. Reppe, Justus Liebig’s Ann. Chem., 582, 1 (1953); W. Reppe and H. Vetter, ibid, 582, 133 (1953).
J. Falbe, Carbon Monoxide in Organic Synthesis, Chapter 2, Springer-Verlag, Berlin, 1970.
A. Mullen, in New Syntheses with Carbon Monoxide ( J. Falbe, Ed.), Springer-Verlag, Berlin, 1980, p. 243.
P. Pino, F. Piacenti and M. Bianchi, in Organic Syntheses via Metal Carbonyls, Vol. 2, ( I. Wender and P. Pino, Eds.) Wiley, New York, 1977, p. 233.
F. Piacenti, M. Bianchi and R. Lazzaroni, Chim. Ind. (Milan) 50, 318 (1968).
L. Cassar, G. P. Chiusoli and F. Guerrieri, Synthesis, 509 (1973).
J. Tsuji, Advan. Org. Chem., 6, 109 (1969).
K. Bittler, N. V. Kutepow, D. Neubauer and H. Reis, Angew. Chem., 80, 352 (1968).
J. F. Knifton, J. Org. Chem., 41, 2885 (1976).
E. N. Frankel, F. L. Thomas and W. K. Rohwedder, Advan. Chem. Ser., 132, 145 (1974).
H. Bahrmann, in New Syntheses with Carbon Monoxide ( J. Falbe, Ed.), Springer-Verlag, Berlin, 1980, p. 372.
P. Hofmann, K. Kosswig and W. Schaefer, Ind. Eng. Chem. Prod. Res. Dev., 19, 330 (1980).
R. F. Heck and D. S. Breslow, J. Am. Chem. Soc., 85, 2779 (1963).
R. F. Heck, J. Am. Chem. Soc., 85, 2013 (1963).
J. Tsuji, Ace. Chem. Res., 2, 144 (1969).
J. Tsuji and K. Ohno, Advan. Chem. Ser., 70, 155 (1968).
J. Tsuji, M. Morikawa and J. Kiji, Tetrahedron Letters, 1061 (1963).
J. F. Knifton, J. Org. Chem., 41, 793 (1976).
J. H. Craddock, A. Hershman, F. E. Paulik and J. F. Roth, US Patent,3,816,488 (1974); J. H. Craddock, J. F. Roth, A. Hershman and F. E. Paulik, US Patent,3,989,747 (1976) to Monsanto.
M. E1-Chahawi, U. Prange, W. Vogt and H. Richtzenhain, German Patent,2,639,327 (1977) to Dynamit Nobel.
R. Kummer, H. W. Schneider, F. J. Weiss and O. Lemon, German Patent,2,837,815 (1980) to BASF.
Belgian Patent,770,615 (1972) to BASF.
J. Tsuji, I. Kiji and S. Hosaka, Tetrahedron Letters, 605 (1974).
W. E. Billups, W. E. Walker and T. C. Shields, Chem. Commun., 1067 (1971).
J. Knifton, J. Catal., 60, 27 (1979).
D. M. Fenton and K. L. Olivier, Chem. Tech., 2, 220 (1972).
G. P. Chiusoli, Pure Appl. Chem., 52, 635 (1980).
D. Medema, R. van Helden and C. F. Kohll, Inorg. Chim. Acta, 3, 255 (1969).
D. M. Fenton and P. J. Steinwald, J. Org. Chem., 37, 2034 (1972).
H. S. Kesling,British Patent,2,064,353 (1980) to Atlantic Richfield.
G. Consiglio and P. Pino, Chimia, 30, 193 (1976).
Y. Iwashita and M. Sakuraba, Tetrahedron Letters, 2409 (1971).
N. von Kutepow, German Patent,2,445,193 (1976) to BASF.
M. El-Chahawi and U. Prange, Chem. Ztg., 102, 1 (1978).
M. El-Chahawi and H. Richtzenhain, German Patent,2,240,398 and 2,240,399 (1974) to Dynamit Nobel.
M. El-Chahawi, U. Prange, H. Richtzenhain and W. Vogt, German Patent,2,553,931 (1977) to Dynamit Nobel.
K. Redecker, M. El-Chahawi, H. Richtzenhain and W. Vogt, German Patent,2,446,657 (1976) to Dynamit Nobel.
M. El-Chahawi, U. Prange, H. Richtzenhain and W. Vogt, German Patent,2,606,655 (1977) to Dynamit Nobel.
A. Schoenberg, I. Bartoletti and R. F. Heck, J. Org. Chem., 39, 3318 (1974).
U. Prange, M. El-Chahawi, H. Richtzenhain and W. Vogt, German Patent,2,557,011 (1977) to Dynamit Nobel.
M. El-Chahawi, H. Richtzenhain and W. Vogt, German Patent,2,410,782 (1975) to Dynamit Nobel.
A. Moro, M. Foa and L. Cassar, British Patent,1,560,609 (1980) to Montedison.
B. Falk, W. Vogt and H. Richtzenhain, German Patent,2,704,191 (1978) to Dynamit Nobel.
U. Prange, M. El-Chahawi, H. Richtzenhain and W. Vogt, German Patent,2,509,017 (1976) to Dynamit Nobel.
Belgian Patent, 877,229 (1979) to Dynamit Nobel.
M. El-Chahawi and H. Richtzenhain, German Patent,2,259,072 (1974) to Dynamit Nobel.
G. P. Chiusoli,Angew. Chem., 72, 74 (1960); Chim. Ind. (Milan) 41, 503 (1959).
F. Montino and M. Caseley, German Patent,1,936,725 (1970) to Montecatini.
U. Prange, H. Richtzenhain and W. Vogt, German Patent,2,436,788 (1976) to Dynamit Nobel.
U. Prange, M. El-Chahawi, H. Richtzenhain and W. Vogt, German Patent,2,524,389 (1976) to Dynamit Nobel.
M. El-Chahawi, U. Prange, H. Richtzenhain and W. Vogt, German Patent,2,403,483 (1375) to Dynamit Nobel.
J. P. Collman, S. R. Winter and R. G. Komoto, J. Am. Chem. Soc., 95, 249 (1973).
J. J. Brunet, C. Sidot and P. Caubere, J. Org. Chem., 46, 3147 (1981); see also B. Loubinoux, B. Fixari, J. J. Brunet and P. Caubere, J. Organometal. Chem., 105, C22 (1976).
J. J. Brunet, C. Sidot and P. Caubere, J. Organometal. Chem., 204, 229 (1980).
J. J. Brunet, C. Sidot, B. Loubinoux and P. Caubere, J. Org. Chem., 44, 2199 (1979).
J. K. Stille and K. S. Y. Lau, Acc.Chenz Res., 10, 434 (1977).
J. K. Stille and P. K. Wong, J. Org. Chem., 40, 532 (1975).
J. K. Stille, L. F. Hines, R. W. Fries, P. K. Wong, D. E. James and K. Lau, Advan. Chem. Ser., 132, 90 (1974).
T. Yukawa, N. Yamakami, M. Honna, Y. Komachiya and H. Wakamatsu, German Patent,2,364,039 (1974) to Ajinomoto.
A. Schoenberg and R. F. Heck, J. Am. Chem. Soc., 96, 7761 (1974).
W. P. Weber and G. W. Gokel, Phase Transfer Catalysis in Organic Synthesis, Springer-Verlag, Berlin, 1977.
C. M. Starks and C. Liotta, Phase Transfer Catalysis, Principles and Techniques, Academic Press, New York, 1978.
H. Alper, Advan. Organometal. Chem., 19, 183 (1981).
L. Cassar, in Fundamental Research in Homogeneous Catalysis ( M. Tsutsui and R. Ugo, Eds.), Plenum Press, New York, 1977, p. 115.
H. Alper and H. des Abbayes, J. Organometal Chem., 134, C11 (1977).
L. Cassar and M. Foa, J. Organometal. Chem., 134, C15 (1977).
L. Cassar and M. Foa, German Patent,2,801,886 (1978) to Montedison.
H. des Abbayes and A. Buloup, Tetrahedron Letters, 21, 4393 (1980).
H. des Abbayes and A. Buloup, J. Organometal, Chem., 179, C21 (1979).
S. Gambarotta and H. Alper, J. Organometal, Chem., 212, C23 (1981).
S. Gambarotta and H. Alper, J. Organometal. Chem., 194, C19 (1980).
J. J. Brunet, C. Sidot and P. Caubere, Tetrehedron Letters, 1013 (1981).
L. Cassar, M. Foa and A. Gardano, J. Organometal. Chem., 121, C55 (1976).
L. Cassar, M. Foa and A. Gardano, US Patent,4,034,004 (1977) to Montedison.
N. N. Crounse, Org. React., 5, 290 (1949).
W. F. Gresham and G. E. Tabet, US Patent,2,485,237 (1949) to Du Pont.
S. Fujiyama and T. Kasahara, Hydrocarbon Process., 57 (11), 147 (1978).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1983 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Sheldon, R.A. (1983). Olefin Carbonylation and Related Reactions. In: Chemicals from Synthesis Gas. Catalysis by Metal Complexes, vol 3. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-1019-0_5
Download citation
DOI: https://doi.org/10.1007/978-94-017-1019-0_5
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-8378-4
Online ISBN: 978-94-017-1019-0
eBook Packages: Springer Book Archive