C 2 -Symmetrical 3,4-Ethylenedioxythiophene Monomers through a Divergent Approach.

Autor:	Martinelli A; Department of Chemistry and INSTM Research Unit, University of Pavia, Via Torquato Taramelli 12, 27100 Pavia, Italy., Nitti A; Department of Chemistry and INSTM Research Unit, University of Pavia, Via Torquato Taramelli 12, 27100 Pavia, Italy., Po R; New Energies, Renewable Energies and Materials Science Research Center, Eni S.p.A., Via Giacomo Fauser 4, 28100 Novara, Italy., Pasini D; Department of Chemistry and INSTM Research Unit, University of Pavia, Via Torquato Taramelli 12, 27100 Pavia, Italy.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2024 Mar 15; Vol. 89 (6), pp. 4237-4243. Date of Electronic Publication: 2024 Feb 29.
DOI:	10.1021/acs.joc.3c02972
Abstrakt:	We present a divergent synthetic approach to C 2 -symmetrical 3,4-Ethylenedioxythiophene (EDOT) monomers in which functionalities can be introduced as pendant chains from the ethylene bridge. The key synthon, obtained through a high yielding trans -etherification, is the chiral EDOT with bromomethyl pendant groups and is prone to substitution reactions with oxygen-based nucleophiles. Elimination of the key precursor affords a diene that can be elaborated into unprecedented PhEDOT monomers using the Diels-Alder reaction. The strategy is further validated by the synthesis of a dithiane-containing EDOT.
Databáze:	MEDLINE
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