Issue 97, 2020

Diels–Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene S,S-dioxides: an unprecedented de-oxygenation vs. sulfur dioxide extrusion

Abstract

Diels–Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene dioxides in xylenes at reflux led to the formation of tetra aryl-substituted dibenzothiophene as well as penta aryl-substituted benzene analogues depending on the influence of aryl substituents present on cyclopentadienones. The intermediate dihydrodibenzothiophene-dioxides underwent aromatization either through de-oxygenation or extrusion of sulfur dioxide to furnish substituted dibenzothiophenes or benzenes.

Graphical abstract: Diels–Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene S,S-dioxides: an unprecedented de-oxygenation vs. sulfur dioxide extrusion

Supplementary files

Article information

Article type
Communication
Submitted
28 Aug 2020
Accepted
05 Nov 2020
First published
06 Nov 2020

Chem. Commun., 2020,56, 15317-15320

Diels–Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene S,S-dioxides: an unprecedented de-oxygenation vs. sulfur dioxide extrusion

P. Manikandan, J. Karunakaran, E. Varathan, G. Schreckenbach and A. K. Mohanakrishnan, Chem. Commun., 2020, 56, 15317 DOI: 10.1039/D0CC05842D

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