Abstract
The decarbonylation of aldehydes, acyl halides, aroyl halides, alcohols, or ketones is a useful and important reaction in organic synthesis. (1,2,3) Although several methods not utilizing transition metals are known(4,5) (including various deformylation reactions and thermal and photochemical decarbonylations), they are not general and not usually applicable under mild conditions where undesirable side reactions are minimized.(1)
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References
J. Tsuji and K. Ohno, Synthesis 1, 157 (1969).
C. W. Bird, Transition Metal Intermediates in Organic Synthesis (Logos Press, London, 1967 ), pp. 112, 239.
A. Kozikowski and H. Wetter, Synthesis 1976, 561.
W. M. Schubert and R. R. Kinther, The Chemistry of the Carbonyl Group ( WileyInterscience of John Wiley and Sons, New York, 1966 ), p. 695.
J. N. Pitts and J. K. S. Wan, The Chemistry of the Carbonyl Group ( Wiley-Interscience of John Wiley and Sons, New York, 1966 ), p. 823.
J. Chatt and B. L. Shaw, Chem. and Ind. 1960, 931.
J. Chatt and B. L. Shaw, Chem. and Ind. 1961, 290.
L. Vaska and J. W. DiLuzio, J. Am. Chem. Soc. 83, 1262 (1961).
L. Vaska, Chem. and Ind. 1961, 1402.
J. Chatt, B. L. Shaw, and A. E. Field, J. Chem. Soc. 1964, 3466.
L. Vaska and J. W. DiLuzio, J. Am. Chem. Soc. 83, 2784 (1961).
J. P. Collman, C. I. Sears, and M. Kubota, Inorg. Synthesis 11, 101 (1968).
L. Vaska, J. Am. Chem. Soc. 86, 1943 (1964).
R. H. Prince and K. A. Raspin, J. C. S., Chem. Comm. 1966, 156.
R. H. Prince and K. A. Raspin, J. Chem. Soc. (A) 1969, 612.
R. H. Prince and K. A. Raspin, J. Inorg. Nucl. Chem. 31, 695 (1969).
K. A. Raspin, J. Chem. Soc. (A) 1969, 461.
N. W. Alcock and K. A. Raspin, J. Chem. Soc. (A) 1968, 2108.
J. Blum, S. Kraus, and Y. Pickholtz, J. Organomet. Chem. 33, 18 (1971).
a) M. C. Baird, C. J. Nyman, and G. W. Wilkinson, J. Chem. Soc. (A) 1969, 346; (b) M. C. Baird, J. T. Mague, J. A. Osborn, and G. Wilkinson, J. Chem. Soc. (A) 1967, 1347.
J. Blum, E. Oppenheimer, and E. D. Bergman, J. Am. Chem. Soc. 89, 2338 (1967).
K. Ohno and J. Tsuji, J. Am. Chem. Soc. 90, 99 (1968).
J. K. Stille, M. T. Regan, R. W. Fries, F. Huang, and T. McCarley, Adv. Chem. Ser. 132, 181 (1974).
a) J. K. Stille and M. T. Regan, J. Am. Chem. Soc. 96, 1508 (1974); (b) J. K. Stille and R. W. Fries, J. Am. Chem. Soc. 96, 1514 (1974); (c) J. K. Stille, F. Huang, and M. T. Regan, J. Am. Chem. Soc. 96, 1518 (1974).
A. Rusina and A. A. Vlcek, Nature 206, 295 (1965).
E. Muller, A. Segnitz, and E. Langer, Tetrahedron Lett. 1969, 1169.
Y. S. Varshavskii, E. P. Shestakova, N. A. Buzina, T. G. Cherkasova, N. V. Kiseleva, and V. A. Kormer, Koord. Khim. 2, 1410 (1976); through Chem. Abstr. 86, 37002 (1977).
Y. S. Varshavskii, E. P. Shestakova, N. V. Kiseleva, T. G. Cherkasova, N. A. Buzina, L. S. Bresler, and V. A. Kormer, J. Orgnomet. Chem. 170, 81 (1979).
J. J. Alexander and A. Wojcicki, Inorg. Chem. 12, 74 (1973).
J. J. Alexander and A. Wojcicki, J. Organomet. Chem. 15, C23 (1968).
F. H. Jardine, Progress in Inorganic Chemistry, edited by S. J. Lippard, Vol. 28, pp. 63–202 ( Wiley-Interscience of John Wiley and Sons, New York 1981 ).
G. Gomazetis, B. Tarpey, D. Dolphin, B. R. James, J. C. S., Chem. Commun. 1980, 939.
K. S. Y. Lau, Y. Becker, F. Huang, N. Baenziger, and J. K. Stille, J. Am. Chem. Soc. 99, 5664 (1977).
D. L. Egglestone, M. C. Baird, C. J. L. Lock, and G. Turner, J. C. S., Dalton 1977, 1576.
J. A. Osborn, F. H. Jardine, and G. Wilkinson, J. Chem. Soc. (A) 1966, 1711.
M. C. Baird, C. J. Nyman, and G. Wilkinson, J. Chem. Soc. (A) 1968, 348.
J. A. Kampmeier, R. M. Rodehorst, and J. B. Philip, Jr., J. Am. Chem. Soc. 103, 1847 (1981).
J. B. Philip, r-, Ph.D. Thesis, University of Rochester, 1980.
J. A. Kampmeier, S. H. Harris, and D. K. Wedegaertner, J. Org. Chem. 45, 315 (1980).
J. K. Stille, M. T. Regan, R. W. Fries, F. Huang, and T. McCarley, Adv. Chem. Series 132, 181 (1974).
J. A. Kampmeier, S. H. Harris, and R. M. Rodehorst, J. Am. Chem. Soc. 103, 1478 (1981).
C. A. Tolman, P. Z. Meakin, D. L. Lindner, and J. P. Jesson, J. Am. Chem. Soc. 9 – 6, 2762 (1974).
J. Halpern and C. S. Wong, J. C. S., Chem. Commun. 1973, 629.
C. S. Wong, Ph.D. Thesis, University of Chicago, 1973.
D. A. Slack, D. L. Egglestone, and M. C. Baird, J. Organomet. Chem. 146, 71 (1978).
N. A. Dunham and M. C. Baird, J. C. S., Dalton 1975, 774.
J. K. Stille, Ann. New York Academy of Science 295, 52 (1977).
J. Blum, Tetrahedron Lett. 1966, 1605.
J. K. Stille, private communication.
P. J. Davidson, M. F. Lappert, and R. Pearce, Chem. Rev. 76, 219 (1976).
M. C. Baird, J. Organomet. Chem. 64, 289 (1974).
J. W. Suggs, J. Am. Chem. Soc. 100, 640 (1978).
H. M. Walborsky and L. E. Allen, J. Am. Chem. Soc. 93, 5465 (1971).
H. M. Walborsky and L. E. Allen, Tetrahedron Lett. 1970, 823.
P. B. Chock and J. Halpern, J. Am. Chem. Soc. 88, 3511 (1966).
J. Y. Chen, Ph.D. Thesis, The University of Chicago, 1972.
R. Ugo, A. Pasini, A. Fusi, and S. Cenini, J. Am. Chem. Soc. 94, 7364 (1972).
W. Strohmeier and P. Prohler, J. Organomet. Chem. 108, 393 (1976).
J. Tsuji and K. Ohno, Tetrahedron Lett. 1966, 4713. j
G. L. Geoffroy, D. A. Denton, M. E. Keeney, and R. R. Bucks, Inorg. Chem. 15, 2382 • (1976).
J. Chatt and B. L. Shaw, J. Chem. Soc. (A) 1966, 1437.
D. H. Doughty and L. H. Pignolet, J. Am. Chem. Soc. 100, 7083 (1978).
D. H. Doughty, M. F. McGuiggan, H. Wang, and L. H. Pignolet, Fundamental Research in Homogeneous Catalysis 3, 909 (1979).
D. H. Doughty, M. P. Anderson, A. L. Casalnuovo, M. F. McGuiggan, C. C. Tso, H. H. Wang, and L. H. Pignolet, Adv. Chem. Ser. 196, 65 (1982).
R. R. Schrock and J. A. Osborn, J. Am. Chem. Soc. 93, 2397 (1971).
D. H. Doughty, Ph.D. Thesis, University of Minnesota, 1979.
A. S. C. Chan, J. J. Pluth, and J. Halpern, J. Am. Chem. Soc. 102, 5952 (1980).
M. D. Fryzuk and B. Bosnich, J. Am. Chem. Soc. 99, 6262 (1977).
W. S. Knowles, M. J. Sabacky, and B. D. Vineyard, Adv. Chem. Ser. 132, 274 (1974).
B. R. James and D. Mahajan, Can. J. Chem. 57, 180 (1979).
J. Halpern, D. P. Riley, A. C. S. Chan, and J. J. Pluth, J. Am. Chem. Soc. 99, 8055 (1977).
H. H. Wang, Ph.D. Thesis, University of Minnesota, 1981.
J. Y. Chen, Ph.D. Thesis, University of Chicago, 1972.
M. P. Anderson and L. H. Pignolet, Inorg. Chem. 20, 4101 (1981).
P. S. Chua, N. K. Roberts, B. Bosnich, S. J. Okrasinski, and J. Halpern, J. Chem. Soc., Chem. Comm. 1981, 1278.
S. D. Ittle, C. A. Tolman, A. D. English, and J. P. Jesson, Adv. Chem. Ser. 173, 67 (1979).
C. A. Tolman, S. D. Ittle, A. D. English, and J. P. Jesson, J. Am. Chem. Soc. 100, 4080 (1978).
A. R. Sanger, J. C. S., Dalton 1977, 120.
C. L. U. Su, Adv. Organomet. Chem. 17, 269 (1979).
T. B. Rauchfuss, J. Am. Chem. Soc. 101, 1045 (1979).
J. P. Collman and L. S. Hegedus, Principles and Applications of Organotransition Metal Chemistry ( University Science Books, Mill Valley, CA, 1980 ).
Y. Kawabata, T. Hayashi, and I. Ogata, J. C. S., Chem. Commun. 1975, 462.
J.-C. Poulin, T.-P. Dang, and H. B. Kagan, J. Organomet. Chem. 84, 87 (1975).
W. J. Knebel and R. J. Angelici, Inorg. Chem. 13, 627, 632 (1974).
L. H. Pignolet, D. H. Doughty, S. C. Nowicki, M. P. Anderson, and A. L. Casalnuovo, J. Organomet. Chem. 202, 211 (1980).
J. P. Collman and L. S. Hegedus, Principles and Applications of Organotransition Metal Chemistry ( University Science Books, Mill Valley, CA, 1980 ), p. 211.
J. P. Collman and L. S. Hegedus, Principles and Applications of Organotransition Metal Chemistry ( University Science Books, Mill Valley, CA, 1980 ), p. 205.
M. P. Anderson, B. J. Johnson, and L. H. Pignolet, preliminary results.
L. H. Pignolet, D. H. Doughty, S. C. Nowicki, and A. L. Casalnuovo, Inorg. Chem. 19, 2172 (1980).
M. F. McGuiggan, D. H. Doughty, and L. H. Pignolet, J. Organomet. Chem. 185, 241 (1980).
M. F. McGuiggan, Ph.D. Thesis, University of Minenesota, 1982.
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Doughty, D.H., Pignolet, L.H. (1983). Decarbonylation Reactions Using Transition Metal Complexes. In: Pignolet, L.H. (eds) Homogeneous Catalysis with Metal Phosphine Complexes. Modern Inorganic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-3623-5_11
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