The formation and decomposition of 1,4,8,11-tetra-azacyclotetradeca-4,11-dienes

Olga H. Hankovszky, Kálmán Hideg, Douglas Lloyd, Hamish McNab

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Abstract

When ethylenediamine reacts with benzylideneacetone the final product isolated is a tetra-azacyclotetradecadiene (4) but the reaction path is complex and proceeds via an equilibrium mixture containing two macrocycles, a tetra-hydrodiazepine, and a mono-condensation product. If the macrocycle (4) is heated, or left in solution at room temperature, the same equilibrium mixture is generated. Removal of ethylenediamine from this mixture promotes formation of a bisenimine which on addition of ethylenediamine slowly regenerates the equilibrium mixture. The macrocycle (4) is cleaved by hydroxylamine to give an oxime. Some new tetra-azacyclotetradecadienes have been prepared. The reaction between neat ethylenediamine and enones, previously reported to provide tetrahydro-diazepines, gives either macrocycles or bisoxoenamines as the isolated products.

Original languageEnglish
Pages (from-to)1345-1350
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - Jan 1 1979

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ASJC Scopus subject areas

  • Chemistry(all)

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