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Issue 12, 2013
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Thermal 8π electrocyclic reaction of heteroarene tetramers: new efficient access to π-extended cyclooctatetraenes

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Abstract

Bromo-substituted acyclic thiazole tetramers selectively underwent an 8π thermal electrocyclic reaction at high temperatures of 280–300 °C without solvent, producing π-extended thiazole-fused cyclooctatetraenes (COTs) in high yields. A quantum chemical study provided a rationale for the lower activation barrier and high selectivity of the 8π electrocyclic reaction mode over a competitive 6π electrocyclic reaction. The terminal bromine atom acts as a leaving group to trigger the rearomatization of the electrocyclized intermediate, which leads to the formation of the energetically stable COT products. This synthetic protocol enables us to synthesize a series of thiazole-fused COTs, including a derivative that can form loosely stacked columnar arrays in the crystalline state and shows fluorescence in the solid state.

Graphical abstract: Thermal 8π electrocyclic reaction of heteroarene tetramers: new efficient access to π-extended cyclooctatetraenes

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Supplementary files

Article information


Submitted
09 Aug 2013
Accepted
10 Sep 2013
First published
11 Sep 2013

Chem. Sci., 2013,4, 4465-4469
Article type
Edge Article

Thermal 8π electrocyclic reaction of heteroarene tetramers: new efficient access to π-extended cyclooctatetraenes

K. Mouri, S. Saito, I. Hisaki and S. Yamaguchi, Chem. Sci., 2013, 4, 4465
DOI: 10.1039/C3SC52232F

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