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Issue 17, 2012
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Chemistry of 9,10-phenanthrenequinone revisited: iron(iii) chloride catalyzed reactions of 9,10-phenanthrenequinone with acyclic and cyclic ketones provide furan annulated products

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Abstract

9,10-Phenanthrenequinone (PQ) reacts with ketones under FeCl3 catalysis to furnish a variety of structurally diverse furan annulated products. While the reaction of PQ with acetone and cyclopentanone furnishes furan annulated ketals, its reaction with ethyl alkyl ketones provides 3-furaldehyde annulated products. In contrast to the reaction of PQ with cyclopentanone, its reaction with cyclohexanone furnishes a tetrahydrobenzofuran annulated secondary alcohol. The reactions of PQ with cycloheptanone and cyclooctanone take a different course to provide 7,8-dihydro-6H-cyclohepta[b]furan and 6,7,8,9-tetrahydrocycloocta[b]furan annulated products, respectively. Mechanistically, the above reactions go through aldol condensation, dehydration and cyclization to form furan-phenanthrene annulated products where in each step FeCl3 catalysis is involved.

Graphical abstract: Chemistry of 9,10-phenanthrenequinone revisited: iron(iii) chloride catalyzed reactions of 9,10-phenanthrenequinone with acyclic and cyclic ketones provide furan annulated products

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Article information


Submitted
17 Mar 2012
Accepted
26 May 2012
First published
28 May 2012

RSC Adv., 2012,2, 6773-6783
Article type
Paper

Chemistry of 9,10-phenanthrenequinone revisited: iron(III) chloride catalyzed reactions of 9,10-phenanthrenequinone with acyclic and cyclic ketones provide furan annulated products

H. Surya Prakash Rao and S. Vijjapu, RSC Adv., 2012, 2, 6773
DOI: 10.1039/C2RA20499A

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