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Synthesis of dithiafulvene-quinone donor-acceptor systems: isolation of a Michael adduct
Henriette Lissau1, Martyn Jevric1, Anders Østergaard Madsen1
1Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark.
Abstract:
π-Conjugated donor-acceptor systems based on dithiafulvene (DTF) donor units and various acceptor units have attracted attention for their linear and nonlinear optical properties. The reaction between p-benzoquinone and a 1,3-dithiole phosphonium salt, deprotonated by lithium hexamethyldisilazide (LiHMDS), gave a product mixture from which the Michael adduct [systematic name: dimethyl 2-(3-hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene)-2H-1,3-dithiole-4,5-dicarboxylate], C13H10O6S2, was isolated. It is likely that one of the unidentified products obtained previously by others from related reactions could be a similar Michael adduct.
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