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Tetrahedron Letters

Volume 54, Issue 10, 6 March 2013, Pages 1227-1229
Tetrahedron Letters

Self sensitized photooxidation of tetrathienyltetrathiafulvalenes: synthesis of thienyl substituted 1,2,5,8-tetrathiecine-6,7-dione, a new heterocyclic system

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Abstract

Irradiation of tetrathienyltetrathiafulvalenes in an oxygen saturated solution gives tetrathienyl substituted 1,2,5,8-tetrathiecine-6,7-diones, via singlet oxygen generation followed by cycloaddition onto the TTF double bond and a final rearrangement process. The thermal and photochemical behaviour and reductive methylation of this new class of macro-heterocyclic system have also been investigated.

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Acknowledgments

The work was financially supported by the PRIN Project 2009. We would like to thank Professor G. L. Giorgi for ES-MS analysis, Dr Iacopo Barbetti for laboratory experimental assistance and the Centro di Analisi e Determinazioni Strutturali of the University of Siena for X-ray data collection.

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