Studies on calix(aza)crowns. Part II. Synthesis of novel proximal Doubly bridged calix[4]arenes by intramolecular ring closure of syn 1,3-and 1,2-ω- chloroalkylamides

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Abstract

Inherently, chiral calix[4]arenes (9,10) with carboxamidc bridges spanning the proximal positions on the lower rim and 18 achiral counterparts have been synthesized by double intramolecular cyclization of 7b,8b 1,3-and 17 1,2-bis-chloroalkylamides. The conformational analysis of the 1,3- and 1,2-disubstituted calixarene intermediates 5-8 and 15-17 proved an equilibrium of two distorted cone conformations. The success of ring closure was strictly dependent on the chain length of the open chain precursors.

Original languageEnglish
Pages (from-to)3857-3870
Number of pages14
JournalTetrahedron
Volume54
Issue number15
DOIs
Publication statusPublished - Apr 9 1998

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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