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Reactions of acenaphthenequinone and aceanthrenequinone with arenes in superacid

Paper ID Volume ID Publish Year Pages File Format Full-Text
43412 45968 2008 5 PDF Available
Title
Reactions of acenaphthenequinone and aceanthrenequinone with arenes in superacid
Abstract

The hydroxyalkylation reactions of aceanthrenequinone (6) and acenapthenequinone (7) with a series of arenes have been studied. In reactions with the Brønsted superacid CF3SO3H (triflic acid), the condensation products are formed in good yields (58–99%, 10 examples) with high regioselectivity. Computational studies were also done to examine the structures and energies of mono- and diprotonated species from 6 and 7. The results from the condensation reactions are consistent with the formation of superelectrophilic species involving protosolvation of carboxonium ion intermediates.

Graphical abstractThe hydroxyalkylation reactions of aceanthrenequinone (6) and acenapthenequinone (7) with a series of arenes have been studied. In reactions with the Brønsted superacid CF3SO3H, the condensation products are formed in good yields (58–99%, 10 examples) with high regioselectivity. The results from the condensation reactions and also theoretical calculations are consistent with the formation of superelectrophilic species. Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Superacid; Superelectrophile; Condensation; Quinone
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 336, Issues 1–2, 1 March 2008, Pages 128–132
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
You save - $31
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