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Synthesis and photochemical reactivity towards the Paternó–Büchi reaction of benzo[b]furan derivatives: their use in the preparation of 3-benzofurylmethanol derivatives

Paper ID Volume ID Publish Year Pages File Format Full-Text
28934 44107 2007 6 PDF Available
Title
Synthesis and photochemical reactivity towards the Paternó–Büchi reaction of benzo[b]furan derivatives: their use in the preparation of 3-benzofurylmethanol derivatives
Abstract

4-Amino-2,7-dimethylbenzo[b]furan and 4-chlorobenzo[b]furan have been synthesized. The irradiation of 4-amino-2,7-dimethylbenzo[b]furan in the presence of benzaldehyde gave the corresponding endo adduct. The adduct can be hydrolysed to the corresponding 3-benzofurylmethanol derivative. The irradiation of the same compound in the presence of benzophenone gave the corresponding adduct. 4-Chlorobenzo[b]furan did not react with benzaldehyde while, in the presence of benzophenone, gave the corresponding adduct. The hydrolysis of this adduct gave the corresponding 3-benzofurylmethanol derivative.

Keywords
Benzofuran derivatives; Photochemistry; Paternò–Büchi reaction
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Synthesis and photochemical reactivity towards the Paternó–Büchi reaction of benzo[b]furan derivatives: their use in the preparation of 3-benzofurylmethanol derivatives
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 185, Issue 1, 1 January 2007, Pages 38–43
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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