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Synlett 1991; 1991(12): 916-918
DOI: 10.1055/s-1991-20922
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Dehydration of 2-Hydroxyimines with Dicyclohexylcarbodiimide: An Access to Cyclic Alkenylimines

Elmar Schuster* , Carsten Hesse, Dieter Schumann
  • *Institut für Organische Chemie, TU Berlin, Straße des 17. Juni 135, D-1000 Berlin 12, Germany
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Publication Date:
07 March 2002 (online)

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2-Methyl-1-aza-1-cycloalkenes 1 react with aldehydes and ketones to yield 2-(2-hydroxyalkyl)-1-aza-1-cycloalkenes 3 under basic conditions. The resulting 2-hydroxyimines 3 are easily dehydrated by dicyclohexylcarbodiimide (DCC) with copper(I) chloride as catalyst in refluxing ether to furnish the corresponding 2-(1-alkenyl)-1-aza-1-cycloalkenes 4.