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Synthesis of benzo[1,2-b:4,5-b′]difuran derivatives utilizing concomitant photocyclization and photo-Fries rearrangement reactions

Title
Synthesis of benzo[1,2-b:4,5-b′]difuran derivatives utilizing concomitant photocyclization and photo-Fries rearrangement reactions
Authors
Park K.K.Kim S.-H.Park J.W.
Ewha Authors
박준우
SCOPUS Author ID
박준우scopusscopus
Issue Date
2004
Journal Title
Journal of Photochemistry and Photobiology A: Chemistry
ISSN
1010-6030JCR Link
Citation
Journal of Photochemistry and Photobiology A: Chemistry vol. 163, no. 41276, pp. 241 - 247
Indexed
SCI; SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
A synthetic route for 2,6-dialkyl-3,7-diphenylbenzo[1,2- b :4,5- b ′]difurans 1a-c (a: alkyl = n-C7H15; b: alkyl = CH3; c: alkyl = -(CH2)7Br) from p-dimethoxybenzene utilizing photocyclization and photo-Fries rearrangement reactions is described. Dimethoxybenzene was reacted with benzoyl chloride to obtain 3-benzoyl-4-hydroxyphenyl benzoate 5, and the reaction of 5 with alkyl halides gave 4-alkoxy-3-benzoylphenyl benzoates 6a-c. Photoirradiation of 6a-c followed by dehydration afforded 2-alkyl-6-benzoyl-5-hydroxy-3-phenylbenzofurans 7a-c via concomitant photocyclization and photo-Fries rearrangement. Etherification of 7a-c> with alkyl halides gave 5-alkoxy-2-alkyl-6-benzoyl-3- phenylbenzofurans 11a-c, and photocyclization/dehydration reaction of 11a-c provided 2,6-dialkyl-3,7-diphenylbenzo[1,2- b :4,5- b ′]difuran compounds 1a-c. A cyclophane containing both benzo[1,2- b :4,5- b ′]difuran and naphthalene rings was also prepared by the coupling of 1c with 2,7-dihydroxynaphthalene. © 2004 Elsevier B.V. All rights reserved.
DOI
10.1016/j.jphotochem.2003.12.004
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자연과학대학 > 화학·나노과학전공 > Journal papers
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