Application of the Nicholas reaction to the synthesis of dicobalt hexacarbonyl complexed diyne ethers

Jahangir Amin, Majid Motevalli, Christopher J. Richards

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Addition of propargylic or homopropargylic ynols to dicobalt hexacarbonyl propargylium cations gave the expected ether products of the Nicholas reaction, with the exception of 4-phenyl-3-butyn-1-ol which gave a dihydrofuran due to propargylium cation promoted 5-endo ring-closure. Use of chiral dicobalt hexacarbonyl complexed propargylic ynols as both propargylium cation precursor and nucleophile gave racemic doubly complexed disymmetric diyne ethers, each as a single diastereoisomer. Addition of dicobalt hexacarbonyl complexed 1-phenyl-1-butyne-3-ene to the propargylium cation derived from dicobalt hexacarbonyl complexed 1-phenyl-1-butyn-3-ol, followed by the addition of a nucleophile (NuH), gave double complexed 1,7-diphenyl-3-Nu-5-methylhepta-1,6-diynes (d.r. > 10:1).
Original languageEnglish
Pages (from-to)43-50
Number of pages8
JournalJournal of Organometallic Chemistry
Volume776
Early online date31 Oct 2014
DOIs
Publication statusPublished - 15 Jan 2015

Keywords

  • Alkynes
  • Cobalt
  • Ethers
  • Cations
  • Diastereoselective

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