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Manganese(III) Acetate Catalyzed Oxidative Radical Additions of α-Dicarbonyl Compounds to 1- and 2-Phenylcyclohepta-1,3,5-triene

✍ Scribed by Esra Findik; Mustafa Ceylan

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
222 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Manganese(III) acetate catalyzed oxidative radical‐addition reactions of α‐dicarbonyl compounds such as methyl acetoacetate (6), acetylacetone (7), and dimedone (8) to the mixture of 1‐ and 2‐phenylcyclohepta‐1,3,5‐triene (4 and 5) were investigated (Scheme 1). The 1‐phenylcyclohepta‐1,3,5‐triene (4) formed mainly [2+3] and [4+3] dihydrofuran addition products derived from cycloheptatriene and [2+3] dihydrofuran addition products derived from the norcaradiene structure. The 2‐phenylcyclohepta‐1,3,5‐triene (5) formed mainly [6+3] dihydrofuran addition products derived from cycloheptatriene and [4+3] dihydrofuran addition products derived from the norcaradiene structure. The structures of isolated products were established by their spectroscopic data (IR, ^1^H‐ and ^13^C‐NMR, MS, and elemental analysis) and comparison with literature data. The formation mechanism of the products is discussed.

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