Abstract
Gas-liquid phase-transfer catalysis (GL-PTC)1 is a new synthetic organic method that has similarities both with phase-transfer catalysis (PTC)2 and with gas-liquid chromatography (GLC) in that anion transfer processes and partition equilibria between gaseous and liquid phases both take place and affect the synthesis. Using GL-PTC, nucleophilic substitution reactions have been so far carried out under operative conditions and with synthetic results, making this method different from the well known liquid-liquid (LL-) and solid-liquid (SL-) phase-transfer catalysis. As regards these latter, phase-transfer catalysts (onium salts, crown ethers and cryptands) transfer the reactive anion from an aqueous liquid (LL-PTC) or a solid salt (SL-PTC) phase into the organic one in which the substitution reaction occurs. In the case of GL-PTC, where no solvent is used, the catalyst always acts as an anion transfer (between solid and liquid phases) but, as it works in the molten state it also constitutes the medium in which the reaction proceeds.
This is a preview of subscription content, log in via an institution to check access.
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
P.Tundo, J. Org, Chem., 44, 2048 (1979).
a) W. P. Weber and G. W. Gokel, “Phase Transfer Catalysis in Organic Synthesis”, Springer-Verlag, West Berlin, 1977; (b) C. M. Starks and C. Liotta, “Phase Transfer Catalysis”, Academic Press, New York, 1978; (c) E. V. Dehmlov and S. S. Dehmlov, “Phase Transfer Catalysis”, Verlag Chemie, Weiheim, 1980 (d) F. Montanari, D. Landini and F. Rolla, PT Catalyzed Reactions in “Topics in Current Chemistry”, Springer-Verlag, West Berlin, 101, 147 (1981).
D. I. Packham and F. A. Rackley, Chem. Ind.(London), 899(1966).
J. E. Gordon, J. Org. Chem., 30, 2760 (1965).
P. Tundo and P. Venturello, Synthesis, 952 (1979).
a) S. L. Regen and C. Koteel, J. Am. Chem. Soc., 99, 3837(1977); (b) S. L. Regen, S. Quici and S. J. Liaw, J. Org. Chem., 44, 2029(1979); (c) G. Bram and T. Fillebeen-Khan, J. Chem. Soc., Chem. Commun., 522(1979).
E. Angeletti, P. Tundo and P. Venturello, J. Chem. Soc., Perkin I, 993 (1982).
Reference 1c, Chpt. 3, pp. 69–77.
A. Knöchel, J. Oehler and G. Rudolph, Tetrahedron Lett., 3167 (1975).
E. Angeletti, P. Tundo and P. Venturello, J. Chem. Soc., Perkin I, 1137 (1982).
D. Balasubramanian, P. Sukumav and B. Chandani, Tetrahedron Lett., 3543 (1979).
M. Fedorynsky, K. Wojciechowski, Z. Matacz and M. Makosza, J. Org. Chem., 43, 4682 (1978).
E. Angeletti, M. Rubbo, P. Tundo and P. Venturello, submitted for publication.
E. Angeletti, P. Tundo and P. Venturello, J. Chem. Soc., Chem. Commun., 1127 (1980).
P. Tundo, P. Venturello and E. Angeletti, submitted for publication.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1984 Plenum Press, New York
About this chapter
Cite this chapter
Tundo, P., Venturello, P. (1984). Synthetic Reactions by Gas-Liquid Phase-Transfer Catalysis. In: Mathias, L.J., Carraher, C.E. (eds) Crown Ethers and Phase Transfer Catalysis in Polymer Science. Polymer Science and Technology. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-9349-2_19
Download citation
DOI: https://doi.org/10.1007/978-1-4615-9349-2_19
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4615-9351-5
Online ISBN: 978-1-4615-9349-2
eBook Packages: Springer Book Archive