4.12 - 1,3-Dithioles

Add time:09/03/2019    Source:sciencedirect.com

This chapter deals with the synthesis, reactivity, and characterization of five-membered heterocycles containing two sulfur atoms in positions 1 and 3 of the ring, that is, 1,3-dithiolylium ions, mesoionic 1,3-dithiol-4-ones and 4-thiones, 1,3-dithioles, and 1,3-dithiolanes. Aspects of the reactivity of the 1,3-dithiole derivatives concern all synthetic manipulations at ring carbon atoms and heteroatoms as well as at substituents attached to these atoms. A large section is devoted to tetrathiafulvalenes (TTFs) as a special subclass of 1,3-dithioles and π-extended TTFs, due to the great interest of material sciences in these compounds, mainly as semiconductors, organic metals, and superconductors, and progress made in their investigations. New applications of 1,3-dithiole derivatives in organic synthesis, medicine, and bioorganic and enzymatic chemistry are also discussed. An emphasis is also put on theoretical and experimental methods as well as on new procedures for the 1,3-dithiolane protection and deprotection of carbonyl groups, which have been developed in the reviewed period.

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