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Issue 3, 2002
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Synthesis of novel cyclophanes containing both benzo[1,2-b:5,4-b′]difuran and naphthalene rings

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Abstract

Facile routes for the synthesis of novel cyclophanes 1a, b containing both benzo[1,2-b:5,4-b′]difuran and naphthalene rings have been developed. Irradiation of 1,5-dibenzoyl-2,4-dialkoxybenzene derivatives 3a, b with a 350 nm mercury lamp followed by dehydration afforded benzo[1,2-b:5,4-b′]difuran ring systems 5a, b. The cyclophanes 1a, b were prepared either from the ether-forming reaction between the preformed benzodifuran ring derivatives 5a, b and 2,7-dihydroxynaphthalene, or from the photocyclization–dehydration reaction of the macrocycles 6a, b prepared by reacting 1,5-dibenzoyl-2,4-bis(ω-bromoalkoxy)benzene with 2,7-dihydroxynaphthalene. The cyclophanes 2a, b containing two benzo[1,2-b:5,4-b′]difuran and two naphthalene moieties were obtained as minor products.

Graphical abstract: Synthesis of novel cyclophanes containing both benzo[1,2-b:5,4-b′]difuran and naphthalene rings

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Article information


Submitted
12 Nov 2001
Accepted
17 Dec 2001
First published
11 Jan 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 310-314
Article type
Paper

Synthesis of novel cyclophanes containing both benzo[1,2-b:5,4-b′]difuran and naphthalene rings

K. K. Park, H. Lim, S. Kim and D. H. Bae, J. Chem. Soc., Perkin Trans. 1, 2002, 310
DOI: 10.1039/B110312A

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