Study of O-Allylation Using Triazine-Based Reagents

Chem Pharm Bull (Tokyo). 2017;65(1):112-115. doi: 10.1248/cpb.c16-00744.

Abstract

Acid-catalyzed allylating reagent 2,4,6-tris(allyloxy)-1,3,5-triazine (TriAT-allyl) and its substituted derivatives have been developed. The reaction of acid-, and alkali-labile alcohols with these reagents in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) afforded the corresponding allyl ethers in good yields. Reactions using these reagents with an unsymmetrically-substituted regioisometric allyl group suggested that a single isometric allylic cation species would be involved.

MeSH terms

  • Catalysis
  • Mesylates / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Triazines / chemical synthesis*
  • Triazines / chemistry

Substances

  • Mesylates
  • Triazines
  • 2,4,6-tris(allyloxy)-1,3,5-triazine
  • trifluoromethanesulfonic acid