An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones

Figen Turksoy, John D. Wallis, Umit Tunca, Turan Ozturk*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCH 2S)-1,3-dithiole-2-thiones (R=Ph, 4-MeOC6H4, 4-Br C6H4, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discussed in some detail. The new fused dithioles have been converted to novel series of fused TTF derivatives.

Original languageEnglish
Pages (from-to)8107-8116
Number of pages10
JournalTetrahedron
Volume59
Issue number41
DOIs
Publication statusPublished - 6 Oct 2003

Keywords

  • 1,4-dithiin
  • 1,8-diketone ring formation
  • BEDT-TTF
  • Thiophene
  • TTF

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