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Synthesis of dithiafulvene–quinone donor–acceptor systems: isolation of a Michael adduct
Author(s) -
Lissau Henriette,
Jevric Martyn,
Madsen Anders Østergaard,
Nielsen Mogens Brøndsted
Publication year - 2015
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229615008578
Subject(s) - adduct , michael reaction , deprotonation , acceptor , chemistry , quinone , phosphonium salt , phosphonium , medicinal chemistry , polymer chemistry , salt (chemistry) , organic chemistry , catalysis , ion , physics , condensed matter physics
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)‐2 H ‐1,3‐dithiole‐4,5‐dicarboxylate], C 13 H 10 O 6 S 2 , was isolated. It is likely that one of the unidentified products obtained previously by others from related reactions could be a similar Michael adduct.