4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent

4-Cyano-3-oxotetrahydrothiophene (c-THT) has much more to offer than just a platform to various heterocyclic scaffolds. This solid, bench-stable and commercially available reagent can be readily transformed into thioglycolic acid and acrylonitrile upon simple addition of a hydroxide anion. This inte...

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Main Authors: François Richard, Carlos Mateos, Stellios Arseniyadis
Format: Article
Language:English
Published: Georg Thieme Verlag KG 2021-01-01
Series:SynOpen
Subjects:
Online Access:http://www.thieme-connect.de/DOI/DOI?10.1055/s-0040-1706019
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author François Richard
Carlos Mateos
Stellios Arseniyadis
author_facet François Richard
Carlos Mateos
Stellios Arseniyadis
author_sort François Richard
collection DOAJ
description 4-Cyano-3-oxotetrahydrothiophene (c-THT) has much more to offer than just a platform to various heterocyclic scaffolds. This solid, bench-stable and commercially available reagent can be readily transformed into thioglycolic acid and acrylonitrile upon simple addition of a hydroxide anion. This interesting feature enables its use as a particularly versatile acrylonitrile anion surrogate.
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spelling doaj.art-b907ed0bc03f4da099ca89d4a053d2ec2022-12-21T21:27:34ZengGeorg Thieme Verlag KGSynOpen2509-93962021-01-010501252810.1055/s-0040-17060194-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion EquivalentFrançois Richard0Carlos Mateos1Stellios Arseniyadis2Queen Mary University of London, School of Biological and Chemical SciencesCentro de Investigación Lilly S.A.Queen Mary University of London, School of Biological and Chemical Sciences4-Cyano-3-oxotetrahydrothiophene (c-THT) has much more to offer than just a platform to various heterocyclic scaffolds. This solid, bench-stable and commercially available reagent can be readily transformed into thioglycolic acid and acrylonitrile upon simple addition of a hydroxide anion. This interesting feature enables its use as a particularly versatile acrylonitrile anion surrogate.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0040-1706019acrylonitrilesurrogateheterocyclealkylationmichael additionpalladiumretro-dieckmann
spellingShingle François Richard
Carlos Mateos
Stellios Arseniyadis
4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent
SynOpen
acrylonitrile
surrogate
heterocycle
alkylation
michael addition
palladium
retro-dieckmann
title 4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent
title_full 4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent
title_fullStr 4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent
title_full_unstemmed 4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent
title_short 4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent
title_sort 4 cyano 3 oxotetrahydrothiophene c tht an ideal acrylonitrile anion equivalent
topic acrylonitrile
surrogate
heterocycle
alkylation
michael addition
palladium
retro-dieckmann
url http://www.thieme-connect.de/DOI/DOI?10.1055/s-0040-1706019
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