Specific features of the chemical behavior of acetylenic derivatives of benzocrown ethers

S. V. Klyatskaya, E. V. Tretyakov, S. F. Vasilevsky

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

4′-Ethynylbenzo-12-crown-4 (8), 4′-ethynylbenzo-15-crown-5 (9), and 4′-ethynylbenzo-18-crown-6 (10) were synthesized by cross-coupling of the corresponding aryl iodides 1-3 with 2-methylbut-3-yn-2-ol (4a) followed by the retro-Favorsky cleavage of the resulting carbinols. Unlike the corresponding benzo-12-crown-4 derivative (5a), the cleavage of tertiary acetylenic alcohols of benzo-15-crown-5 (6a) and benzo-18-crown-6 (7a) requires more than one molar equivalent of KOH. Aminoalkylation of crown ether 8 gives Mannich bases, independently of the reaction conditions and the nature of amine. The aminomethylation of acetylenic crown ethers 9 and 10 with paraform-piperidine (morpholine) in the presence of CuCl yields 1,4-disubstituted buta-1,3-diynes (19, 20) rather than Mannich bases.

Original languageEnglish
Pages (from-to)868-873
Number of pages6
JournalRussian Chemical Bulletin
Volume50
Issue number5
DOIs
Publication statusPublished - 1 Dec 2001
Externally publishedYes

Keywords

  • Alkynes
  • Benzocrown ethers
  • Crown effect
  • Frank-Meister-Hay modification
  • The Mannich reaction
  • The retro-Favorsky reaction

ASJC Scopus subject areas

  • Chemistry(all)

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