Abstract
It was shown that in systems where diphenylacetonitrile were solubilized in organic-aqueous sodium hydroxide emulsions and micelles that one could obtain appreciable yields of the dehydrodimer by anodic oxidation at platinum electrodes if one used a cationic surfactant. It was also shown that it was possible anodically to dimerize diethyl malonate solubilized in micelles in a 2M sodium carbonate solution using a cationic surfactant if bromide ion was present. Best results in the anodic dimerization of diethyl malonate were obtained in emulsions prepared by adding tetrabutylammonium bromide to an aqueous 2M sodium carbonate solution.
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
R. N. Adams, “Electrochemistry at Solid Electrodes,” Marcel Dekker Inc., New York, N.Y., 1969.
C. K. Mann and K. K. Barnes, “Electrochemical Reactions in Nonaqueous Systems,” M. Dekker, Inc., New York, N.Y., 1970.
A. J. Fry, “Synthetic Organic Electrochemistry,” Harper and Row, New York, N.Y., 1972.
M. M. Baizer, Editor, “Organic Electrochemistry, ”Marcel Dekker, Inc., New York, N.Y., 1973.
M. Rifi and F. H. Covitz, “Introduction to Organic Electrochemistry,” M. Dekker, Inc., New York, N.Y., 1974.
N. L. Weinberg and A. Weissberger, Editors, “Techniques of Electroorganic Synthesis,” Vol. 5, Pt. 1, Wiley - Interscience, New York, N.Y., 1974.
N. L. Weinberg, Editor, “Techniques of Electroorganic Synthesis,” Vol. 5, Pt. 2, Wiley - Interscience, New York, N.Y., 1975.
F. D. Popp and H. P. Schultz, Chem. Rev. 62, 19 (1962).
N. L. Weinberg and H. R. Weinberg, Chem. Rev. 68, 449 (1968).
G. Popp, Org. Chem. Bull. 45 (3), (1973). From Eastman Kodak Co., Rochester, N.Y.
R. H. McKee and C. J. Brockmann, Trans. Electrochem. Soc. 62, 203 (1932).
R. H. McKee and B. G. Gerapostolou, Trans. Electrochem. Soc. 68, 329 (1935).
M. M. Baizer, J. Electrochem. Soc. 111, 215 (1964).
Fr. Fichter, Z. Electrochem. 19, 781 (1913).
Fr. Fichter and R. Stocker, Ber. 47, 2007 (1919).
P. N. Anantharam and H. V. K. Udupa, Extended Abstracts of the Meeting of the Electrochemical Soc. Washington, D.C., May 1976, Abs. No. 283.
J. P. Millington and J. Trotman, Extended Abstracts of the Meeting of the Electrochemical Soc. Washington, D. C., May 1976, Abs. No. 279.
Fr. Fichter and O. Muller, Helvet, Chim. Acta 18, 831 (1935).
Fr. Fichter and G. Schetty, Helvet. Chico. Acta 20, 150 (1937).
C. W. Proudfit and W. G. France, J. Phys. Chem. 46, 42 (1942).
L. Eberson and B. Helgee, B. Chem. Scri. 5, 47 (1974).
L. Eberson and B. Helgee, Acta Chem. Scand. B29, 451 (1975).
C. M. Stark, J. Am. Chem. Soc. 93, 195 (1971).
E. V. Dehmlow, Chemtech 1975 210.
S. Hayano and N. Shinozuka, Bull. Chem. Soc. Japan 42, 1469 (1969).
S. Hayano and N. Shinozuka, Bull. Chem. Soc. Japan 43, 2083 (1970).
S. Hayano and N. Shinozuka, Bull. Chem. Soc. Japan 44, 1503 (1971).
P. G. Westmoreland, R. A. Day, Jr., and A. L. Underwood, Anal. Chem. 44, 737 (1972).
T. Erabi, H. Huira, and M. Tanaka, Bull. Chem. Soc. Japan 48, 1354 (1975).
T. C. Franklin and L. Sidarous, Chem. Comm. 1975 741.
T. C. Franklin and L. Sidarous, Extended Abstracts of the Meeting of the Electrochemical Society in Washington, D.C., May 1976, Abstract No. 305.
S. Terabe and R. Konaka. J. Am. Chem. Soc. 91, 5655 (1969)
F. W. Steuber and K. Dimroth, Chem. Ber. 99, 258 (1966).
E. Juday, J. Org. Chem. 22, 532 (1957).
C. R. Noller “Chemistry of Organic Compounds” p. 879, W. B. Saunders Co., Philadelphia, PA., 1965.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1977 Plenum Press, New York
About this chapter
Cite this chapter
Franklin, T.C., Honda, T. (1977). The Use of Phase Transfer Catalysts with Emulsion and Micelle Systems in Electro-Organic Synthesis. In: Mittal, K.L. (eds) Micellization, Solubilization, and Microemulsions. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-4157-4_8
Download citation
DOI: https://doi.org/10.1007/978-1-4613-4157-4_8
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-4159-8
Online ISBN: 978-1-4613-4157-4
eBook Packages: Springer Book Archive