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

Henriette Schjøtt Lissau; Martyn Jevric; Anders Østergaard Madsen; Mogens Brøndsted Nielsen

doi:10.1107/S2053229615008578

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

Henriette Schjøtt Lissau, Martyn Jevric, Anders Østergaard Madsen, Mogens Brøndsted Nielsen

Kemisk Institut

2 Citationer (Scopus)

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.

Originalsprog	Engelsk
Tidsskrift	Acta Crystallographica Section C
Vol/bind	71
Udgave nummer	6
Sider (fra-til)	452-455
Antal sider	4
ISSN	0108-2701
DOI	https://doi.org/10.1107/S2053229615008578
Status	Udgivet - 1 jun. 2015

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10.1107/S2053229615008578

http://onlinelibrary.wiley.com/doi/10.1107/S2053229615008578/abstract

Citationsformater

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title = "Synthesis of dithiafulvene–quinone donor–acceptor systems: isolation of a Michael adduct",

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.",

author = "Lissau, {Henriette Schj{\o}tt} and Martyn Jevric and Madsen, {Anders {\O}stergaard} and Nielsen, {Mogens Br{\o}ndsted}",

year = "2015",

month = jun,

day = "1",

doi = "10.1107/S2053229615008578",

language = "English",

volume = "71",

pages = "452--455",

journal = "Acta crystallographica. Section C, Structural chemistry",

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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 -

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

Abstract

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