Synthesis of dithiafulvene–quinone donor–acceptor systems: isolation of a Michael adduct

TY - JOUR

T1 - Synthesis of dithiafulvene–quinone donor–acceptor systems

T2 - isolation of a Michael adduct

AU - Lissau, Henriette Schjøtt

AU - Jevric, Martyn

AU - Madsen, Anders Østergaard

AU - Nielsen, Mogens Brøndsted

PY - 2015/6/1

Y1 - 2015/6/1

N2 - 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.

AB - 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.

U2 - 10.1107/S2053229615008578

DO - 10.1107/S2053229615008578

M3 - Journal article

C2 - 26044325

SN - 2053-2296

VL - 71

SP - 452

EP - 455

JO - Acta crystallographica. Section C, Structural chemistry

JF - Acta crystallographica. Section C, Structural chemistry

IS - 6

ER -