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Original Articles

Heteropolyacene with Thianthrenium Ring Systems Proving π Electron Delocalization over S Atoms

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Pages 655-670 | Received 01 Jan 2003, Published online: 07 Feb 2007
 

Abstract

The superacid-induced condensation of o-methylsulfinylated thiophenyl(ene) compounds under dilute conditions induces an intramolecular electrophilic ring-closing reaction of a hydroxysulfonium cation onto the adjacent benzene ring to yield the thianthrenium ring systems, which disclose π electron delocalization over sulfonio linkages demonstrating the efficacy of planarization of the benzene rings for the p-π/d-π interaction in arylsulfonium moieties. Crystal structure of the thianthrenium salt reveals that the S+–C(phenyl) bond is significantly shortened upon the ring closing as a result of the increased bond order by the resonance effect.

Acknowledgments

This work was partially supported by a Grant-in-Aid for Scientific Research (No. 14703029) from MEXT, Japan.

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