AlCl3-mediated aldol cyclocondensation of 1,6- and 1,7-diones to cyclopentene and cyclohexene derivatives

Yuji Miyahara, Yoshio N. Ito

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Exactly 1/3 mol of AlCl3 is sufficient to cyclize 1 mol of 1,?-dibenzoylbutane (or pentane) to a cyclopentenone (or hexenone) derivative in high yield at room temperature in 40 min to several hours. This condensation is driven by removing elements of water as HCl and Al(OH)3, and the product enones are exclusively unconjugated, unlike the base-catalyzed condensations providing thermodynamically more stable conjugated enones.

Original languageEnglish
Pages (from-to)6801-6807
Number of pages7
JournalJournal of Organic Chemistry
Volume79
Issue number15
DOIs
Publication statusPublished - Jan 1 2014

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Cyclopentanes
Condensation
Derivatives
Water
Temperature
aluminum chloride
cyclohexene
3-hydroxybutanal
cyclopentenone
pentane

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

AlCl3-mediated aldol cyclocondensation of 1,6- and 1,7-diones to cyclopentene and cyclohexene derivatives. / Miyahara, Yuji; Ito, Yoshio N.

In: Journal of Organic Chemistry, Vol. 79, No. 15, 01.01.2014, p. 6801-6807.

Research output: Contribution to journalArticle

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