Issue 27, 2015

A new synthetic route to substituted tetracenes and pentacenes via stereoselective [4+2] cycloadditions of 1,4-dihydro-1,4-epoxynaphthalene and isobenzofuran

Abstract

Stereoselective [4+2] cycloadditions of 1,4-dihydro-1,4-epoxynaphthalene and isobenzofuran were described. Among several possibilities, synexo and/or antiendo isomers were selectively produced depending on the substitution pattern of the reactants. Importantly, the synexo isomer underwent acid promoted aromatization, affording the corresponding tetracene. These findings enabled us to prepare a substituted pentacene with electron withdrawing groups.

Graphical abstract: A new synthetic route to substituted tetracenes and pentacenes via stereoselective [4+2] cycloadditions of 1,4-dihydro-1,4-epoxynaphthalene and isobenzofuran

Supplementary files

Article information

Article type
Communication
Submitted
05 Jan 2015
Accepted
25 Feb 2015
First published
25 Feb 2015

Chem. Commun., 2015,51, 5963-5966

Author version available

A new synthetic route to substituted tetracenes and pentacenes via stereoselective [4+2] cycloadditions of 1,4-dihydro-1,4-epoxynaphthalene and isobenzofuran

S. Eda, F. Eguchi, H. Haneda and T. Hamura, Chem. Commun., 2015, 51, 5963 DOI: 10.1039/C5CC00077G

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