Synthesis and characterisation of N-functionalized enetetramines, and their properties

GOK Y., CETINKAYA E., Ozdemir I., CETINKAYA B., LAPPERT M.

ACTA CHIMICA SLOVENICA, vol.51, no.3, pp.437-446, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 51 Issue: 3
  • Publication Date: 2004
  • Journal Name: ACTA CHIMICA SLOVENICA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.437-446
  • Keywords: enetetramines, imidazole, amino-Claisen rearrangement, ELECTRON-RICH OLEFINS, CARBENE COMPLEXES, CATALYTIC-ACTIVITY, ALKENE METATHESIS, TETRAAMINOETHYLENES, CYCLOISOMERIZATION, CHEMIE
  • Inonu University Affiliated: Yes

Abstract

Two general routes are described for the synthesis of the title compounds from the reaction of, either the dimethyl acetal of N,N'-dimethylformamide and an appropriate N, N'bis(secondary amine), or sodium hydride (or potassium tert-butoxide) and 4,5-dihydroimidazolium salts. N-Functionalized enetetramines (3, 8) having 2-methoxyethyl or allyl substituent on the N-atom have been made. The reaction of this enetetramines with S-8 and Se, gave the corresponding cyclic chalcogeno ureas derivatives (4, 5). Treatment of potassium tert-butoxide with 1,1'-ethylene-3,3'-diallyldiimidazolidinium dibromide (7) afforded, either the enetetramine ( 8), or, alternatively, the amino-Claisen isomer (9). All new compounds were identified by H-1, C-13 NMR, FT-IR and micro analysis.