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

Yuji Miyahara; Yoshio N. Ito

doi:10.1021/jo5006137

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

Yuji Miyahara, Yoshio N. Ito

Organic and Biological Chemistry

Research output: Contribution to journal › Article › peer-review

20 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 language	English
Pages (from-to)	6801-6807
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	79
Issue number	15
DOIs	https://doi.org/10.1021/jo5006137
Publication status	Published - Aug 2014

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo5006137

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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.",

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AU - Ito, Yoshio N.

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AB - 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.

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

Abstract

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