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

Shohei Eda; Fumiaki Eguchi; Hiroshi Haneda; Toshiyuki Hamura

doi:10.1039/c5cc00077g

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

Chem Commun (Camb). 2015 Apr 7;51(27):5963-6. doi: 10.1039/c5cc00077g. Epub 2015 Mar 4.

Authors

Shohei Eda¹, Fumiaki Eguchi, Hiroshi Haneda, Toshiyuki Hamura

Affiliation

¹ Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan. thamura@kwansei.ac.jp.

PMID: 25735234
DOI: 10.1039/c5cc00077g

Abstract

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