Studies on Lewis acid-mediated intramolecular cyclization reactions of allene-ene systems

Chem Pharm Bull (Tokyo). 2000 Mar;48(3):405-9. doi: 10.1248/cpb.48.405.

Abstract

The Lewis acid-mediated reactions of allene-ene compounds, derived from 3-methylcitronellal or dimethyl malonate, were carried out using various Lewis acids such as ethylaluminum dichloride, diethylaluminum chloride, titanium chloride, zinc chloride etherate, or boron trifluoride etherate, affording unexpectedly intramolecular [2+2]cycloaddition products under some particular reaction conditions without any formation of intramolecular ene reaction products.

MeSH terms

  • Aldehydes / chemistry
  • Alkadienes / chemistry*
  • Cyclization
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Malonates / chemistry*
  • Spectrophotometry, Infrared
  • Terpenes / chemistry

Substances

  • Aldehydes
  • Alkadienes
  • Indicators and Reagents
  • Malonates
  • Terpenes
  • methyl malonate