Abstract
The recommendation is developed that all synthetic chemists should always consider pressure as one of the routine variables available to them, along with temperature, solvent, reaction time, catalysts, and so forth. Ideally, equipment should be available both in the 1–5 and 10–20 kbar range, the former for the habitual testing of all reaction steps under increased pressure, and the latter for the more unusual instances in which gigapascal pressures appear to force otherwise reluctant reactions. The hope is that synthetic chemists will learn to optimize yields and conversions with respect to pressure as well as the other variables, and to report the pressure used just as routinely as they report reaction times and temperatures now.
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Footnotes and References
W. J. le Noble, elsewhere in this volume.
Matsumoto has written several extensive and thorough reviews specifically on the topic of synthesis at high pressure; thus, see K. Matsumoto, T. Uchida, and R. M. Acheson, Heterocycles 16, 1367 (1981); K. Matsumoto, A. Sera, and T. Uchida, Synthesis, 1 (1985); K. Matsumoto and A. Sera, ibid., 999 (1985). References to the reviews on the mechanistic aspects may be found here and in Ref. 1.
Y. Okamoto and Y. Shimagawa, Tetrahedron Lett., 317 (1966).
V. J. le Noble and Y. Ogo, Tetrahedron., 26, 4119 (1970).
E. W. Fawcett and R. O. Gibson, J. Chem. Soc., 387 (1934).
M. G. Gonikberg and L. F. Vereschagin, Zh. Fiz. Khim., 23, 1447 (1949)
C. Walling and J. Peisach, J. Am. Chem. Soc., 80, 5819 (1958)
S. W. Benson and J. A. Berson, J. Am. Chem. Soc., 84, 152 (1962).
R. A. Grieger and C. A. Eckert, J. Am. Chem. Soc., 92, 2918, 7149 (1970).
C. A. Stewart, J. Am. Chem. Soc., 93, 4815 (1971 ) and 94, 635 (1972).
C. Brun and G. Jenner, Tetrahedron, 28, 3113 (1972).
W. J. le Noble, Rev. Phys. Chem. Japan, 50, 207 (1980).
H. Takeshita, S. Sugiyama, and T. Hatsui, Bull. Chem. Soc. Jpn., 58, 2490 (1985).
Y. E. Raifel’d, B. S. El’yanow, and S. M. Makin, Izves. Akad. Nauk SSSR, 1090 (1976).
J. van Jouanne, H. Keim, and R. Huisgen, J. Am. Chem. Soc.101, 151 (1979).
W. J. le Noble and R. Mukhtar, J. Am. Chem. Soc., 97, 5938 (1975).
W. G. Dauben, C. R. Kessel, and K. H. Takemura, J. Am. Chem. Soc., 102, 6893 (1980).
J. Jurczak, T. Kozluk, S. Filipek, and C. H. Eugster, Helv. Chim. Acta, 661, 222 (1983).
S. Srivastava, A. P. Marchand, and W. J. le Noble, unpublished observation.
W. H. Jones, E. W. Tristram, and W. F. Benning, J. Am. Chem. Soc., 81, 2151 (1959).
W. G. Dauben and R. A. Bunce, J. Org. Chem., 48, 4642 (1983).
K. Matsumoto, Angew. Chem., Int. Ed. Engl., 20, 770 (1981).
K. Matsumoto, Angew. Chem., Int. Ed. Engl., 21, 922 (1982).
J. E. Rice and Y. Okamoto, J. Org. Chem., 47, 4189 (1982).
W. J. le Noble, J. Am. Chem. Soc., 85, 1470 (1963).
H. P. Kraemer and H. Plieninger, Tetrahedron, 34, 891 (1986).
W. G. Dauben and R. A. Bunce, Tetrahedron Lett., 23, 4875 (1982). See also M. M. Midland and J. A. McLoughlin, J. Org. Chem., 49, 1316 (1984).
W. H. Pirkle, J. R. Hauske, C. A. Eckert, and B. A. Scott, J. Org. Chem., 42, 3101 (1977).
G. Jenner and M. Kellou, Chem. Commun., 851 (1979).
T. Yamada, Y. Manabe, T. Miyazawa, S. Kuwata, and A. Sera, Chem. Commun., 1500 (1984).
M. Pietraszkiewicz, P. Salanski, and J. Jurczak, Chem. Commun., 1184 (1983).
W. G. Dauben, R. A. Bunce, J. M. Gerdes, K. E. Henegar, A. E. Cunningham, and T. B. Ottoboni, Tetrahedron Lett., 24, 5709 (1983).
J. E. Rice and Y. Okamoto, J. Org. Chem., 46, 446 (1981).
W. P. Roberts and G. Shoham, Tetrahedron Lett., 22, 4895 (1981).
W. P. Roberts, S. Srivastava and W. J. le Noble, Industr. Chem. News, 5, 24 (1984).
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le Noble, W.J. (1987). Organic Synthesis at High Pressure. In: van Eldik, R., Jonas, J. (eds) High Pressure Chemistry and Biochemistry. NATO ASI Series, vol 197. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-3827-4_12
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DOI: https://doi.org/10.1007/978-94-009-3827-4_12
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