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The chemistry of enamines -
C. Gardner, V. Kerrigan, J. Rose, B. Weedon (1949)
166. Acetylene reactions. Part I. Aminobutynes from acetylene and primary or secondary aminesJournal of The Chemical Society (resumed)
- Publisher
- Springer Journals
- Copyright
- Copyright © 1998 by Plenum Publishing Corporation
- Subject
- Chemistry; Chemistry/Food Science, general; Inorganic Chemistry; Organic Chemistry
- ISSN
- 1066-5285
- eISSN
- 1573-9171
- DOI
- 10.1007/BF02498165
- Publisher site
- See Article on Publisher Site
Abstract
New rhodium-catalyzed amination reactions of arylacetylenes and cyclohexen-1-ylacetylene in the presence of strong bases with the use of carbon dioxide as an auxiliary are described. Secondary amines attack the terminal carbon atom of the triple bond followed by protonation of the adjacent carbon atom. Alternatively, the reaction can proceed further with the addition of the second alkyne molecule. The conditions for the selective synthesis of enamines (up to 87% yield) or α-substituted propynylamines (up to 86% yield) are reported.
Journal
Russian Chemical Bulletin – Springer Journals
Published: Sep 1, 2006