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Journals / Turkish Journal of Chemistry / 2005 / Cilt: 29 - Sayı: 6

Manganese(III) Acetate Mediated Free Radical Cyclization of 1,3-Dicarbonyl Compounds with Sterically Hindered Olefins

Mehmet YILMAZ
Emre BİÇER and A. Tarık PEKEL
Pages
579–587
Publication Date
2005-06-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Treatment of 1a, 1b and 1c with 1,2-diphenyl-1-pentene 2a resulted in the formation of tetrahydrobenzofuran 3b and 4,5-dihydrofurans 3d and 3f in lower yields.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:The manganese(III) acetate mediated radical cyclization of dimedone 1a, 2,4-pentanedione 1b, ethyl acetoacetate 1c, 1,3-cyclohexanedione 1d and 5-phenyl-1,3-cyclohexanedione 1e with 1,1-diphenyl-1-butene 2a afforded 4,5-dihydrofurans (3c, 3e) and tetrahydrobenzofurans (3a, 3g, 3h) in good yields (55% - 77%).
📊
Key Findings & Data:Additionally, the reactions of trifluoromethyl-group containing 1,3-dicarbonyls, 4,4,4-trifluoro-1-phenylbutane-1,3-dione 1f and 4,4,4-trifluoro-1-thien-2ylbutane-1,3-dione 1g with 2a 3-trifluoroacetyl-4,5-dihydrofurans gave in 74% and 78% yields, respectively.
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Conclusion & Impact:Treatment of 1a, 1b and 1c with 1,2-diphenyl-1-pentene 2a resulted in the formation of tetrahydrobenzofuran 3b and 4,5-dihydrofurans 3d and 3f in lower yields.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Manganese(III) acetate · free radical cyclization · 3-dicarbonyl

Abstract

The manganese(III) acetate mediated radical cyclization of dimedone 1a, 2,4-pentanedione 1b, ethyl acetoacetate 1c, 1,3-cyclohexanedione 1d and 5-phenyl-1,3-cyclohexanedione 1e with 1,1-diphenyl-1-butene 2a afforded 4,5-dihydrofurans (3c, 3e) and tetrahydrobenzofurans (3a, 3g, 3h) in good yields (55% - 77%). Additionally, the reactions of trifluoromethyl-group containing 1,3-dicarbonyls, 4,4,4-trifluoro-1-phenylbutane-1,3-dione 1f and 4,4,4-trifluoro-1-thien-2ylbutane-1,3-dione 1g with 2a 3-trifluoroacetyl-4,5-dihydrofurans gave in 74% and 78% yields, respectively. Treatment of 1a, 1b and 1c with 1,2-diphenyl-1-pentene 2a resulted in the formation of tetrahydrobenzofuran 3b and 4,5-dihydrofurans 3d and 3f in lower yields.

Özet

The manganese(III) acetate mediated radical cyclization of dimedone 1a, 2,4-pentanedione 1b, ethyl acetoacetate 1c, 1,3-cyclohexanedione 1d and 5-phenyl-1,3-cyclohexanedione 1e with 1,1-diphenyl-1-butene 2a afforded 4,5-dihydrofurans (3c, 3e) and tetrahydrobenzofurans (3a, 3g, 3h) in good yields (55% - 77%). Additionally, the reactions of trifluoromethyl-group containing 1,3-dicarbonyls, 4,4,4-trifluoro-1-phenylbutane-1,3-dione 1f and 4,4,4-trifluoro-1-thien-2ylbutane-1,3-dione 1g with 2a 3-trifluoroacetyl-4,5-dihydrofurans gave in 74% and 78% yields, respectively. Treatment of 1a, 1b and 1c with 1,2-diphenyl-1-pentene 2a resulted in the formation of tetrahydrobenzofuran 3b and 4,5-dihydrofurans 3d and 3f in lower yields.

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Cite This Article

YILMAZ, M., PEKEL, E. B. A. A. T. (2005). Manganese(III) Acetate Mediated Free Radical Cyclization of 1,3-Dicarbonyl Compounds with Sterically Hindered Olefins. Turkish Journal of Chemistry, Cilt: 29 - Sayı: 6, 579–587. https://ajindex.com/articles/227793

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