Effect of solvent polarity extremes on the coupling of cyclopropylcarbene-chromium complexes and alkynes: Synthesis of β-alkoxycyclopentadienones, 2-cyclopentene-1,3-diones, and cis 4,5-disubstituted cyclopentenones

✍ Scribed by James W. Herndon; Paren P. Patel

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 241 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02282-4

✦ Synopsis

The reaction between acetylenes and cyclopropylcarbene-chromium complexes in hexane affords exclusively cyclopentadienone derivatives in good yield, which are readily hydrolyzed to cyclopentenediones. The analogous reaction in 50:50 water dioxane affords cis disubstituted cyclopentenones.