Ortho-Vinylation Reaction of Phenols

Masahiko Yamaguchi, Akio Hayashi, Masahiro Hirama

Research output: Contribution to journalArticlepeer-review

Abstract

In the presence of SnCl4Bu4N reagent, silyl enol ethers and ketones were α-alkylidenated or α-alkenylated with 1-alkynes. Phenols were ortho-alkenylated using this system. Direct ortfeo-vinylation of phenols was achieved by treating with ethyne (acetylene gas) at ambient pressure. These syntheses involve carbostannylation reaction where α-stannyl ketones or phenoxytins add to alkynyltrichlorotins giving 1,1-bis(stannyl) alkenes. Phenol, Vinylation, Alkenylation, 1-Alkyne, Ethyne, SnCl4-Bu3N, Ketone, Silyl.

Original languageEnglish
Pages (from-to)41-53
Number of pages13
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume54
Issue number4
Publication statusPublished - 1996 Dec 1

Keywords

  • Alkylidenation
  • Alkynyltin
  • Carbostannylation
  • Enol ether
  • Phenoxytin
  • α-stannyl ketone

ASJC Scopus subject areas

  • Organic Chemistry

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