A Comparative Study in Oxidative Free Radical Reactions between 9- Benzylidene-9-H Fluorene Derivatives and β-Dicarbonyl Compounds in the Presence of Mn(OAc)3 and CAN

Author(s): Hulya Demirhan, Mustafa Arslan, Mustafa Zengin, Mustafa Kucukislamoglu.

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 7 , 2011

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The reactions of some 1,3-dicarbonyl compounds with 9-benzylidene-9-H-fluorene derivatives in the presence of manganese(III)acetate and ceric ammonium nitrate (CAN) were searched. 9-benzylidene-9-H-fluorene compounds form mainly [2+3] dipolar cycloaddition products such as dihydrofuran and lactone which are spirally attached to the C-9 position of flourene ring with manganese(III)acetate and oxidative addition products with CAN. The best yield of cyclization products was obtained from the reaction between 2c and 1a-c in both oxidants. The stereochemistry of the products 3d, 4d and 5d was only transformed which has coupling constant 13 Hz.

Keywords: 9-benzylidene-9H-fluorene, cerium(IV) ammonium nitrate (CAN), manganese(III) acetate, radicalic oxidation, β-dicarbonyl compounds, b-dicarbonyl compounds, flourene, β-ketoester, β-ketoamide, β-diketones, Methoxyl

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Article Details

Year: 2011
Page: [488 - 494]
Pages: 7
DOI: 10.2174/157017811796504990
Price: $65

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