Abstract
A series of pyrrolidinoenamines of an alicyclic ketone (1) was subjected to the indirect electrooxidation in NaCN-MeOH using iodide ion as a mediator. It was found that the electrolysis products were dependent on the ring size of the ketone component. For example, the cyclohexanone and cycloheptanone enamines exclusively provided a ring fused cyclopropane aminonitrile (2),whereas the cyclooctanone enamine yielded only the corresponding β-cyanoenamine (4).
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
T. Chiba, M. Okimoto, H. Nagai, Y. Takata, J. Org. Chem., 1979, 44, 3519. see also; T. Shono, Y. Matsumura, H. Hamaguchi, T. Imanishi, K. Yoshida, Bull. Chem. Soc. Jpn., 1978, 86, 2101.
J. Szmuszkovicz, E. Cerda, M. F. Grostic, J. F. Zieserl, Jr., Tetrahedron Lett, 1967, 3969.
C. Kaizer, J. Weinstock, Org. Synth., 1988, 6, 910.
P. A. S. Smith, Org. Reactions, 1946, 3, 337.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1998 Springer Japan
About this paper
Cite this paper
Chiba, T., Saitho, I., Okimoto, M. (1998). Electro-Oxidation of Enamines Using Iodide Ion as a Mediator. In: Torii, S. (eds) Novel Trends in Electroorganic Synthesis. Springer, Tokyo. https://doi.org/10.1007/978-4-431-65924-2_36
Download citation
DOI: https://doi.org/10.1007/978-4-431-65924-2_36
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-65926-6
Online ISBN: 978-4-431-65924-2
eBook Packages: Springer Book Archive