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Communication | Regular issue | Vol 9, No. 8, 1978, pp.1003-1008
Published online, 1st January, 1970
DOI: 10.3987/R-1978-08-1003
The Reaction of Benzylideneacetone with Ethylenediamine. Evidence for the Production of Two Isomeric 1,4,8,11-Tetra-azacyclotetradeca-4,11-dienes

Peter W. R. Caulkett, David Greatbanks, Ralph W. Turner,* and John A. J. Jarvis

*Department of Chemistry, ICI Pharmaceuticals, Mereside, Alderley Park, Macclesfield, Cheshire, SK10 4TG, U.K.

Abstract

The reduction of the 1,4,8,11-tetra-azacyclo-tetradeca-4,11-diene product from benzylidene acetone and ethylenediamine to give two isomeric 1,4,8,11-tetra-azacyclotetradecanes is reported. X-ray data for the condensation product of the minor isomer and glyoxal is described. The assignment of the transoid structure, (9) to the minor isomer suggests that the initial tetra-azacyclotetradeca-4,11-diene is a mixture of the diastereoisomers (2) and (3).