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CC BY-NC-ND 4.0 · SynOpen 2021; 05(01): 25-28
DOI: 10.1055/s-0040-1706019
review

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

François Richard 
a   Queen Mary University of London, School of Biological and Chemical Sciences, London, E1 4NS, UK
,
Carlos Mateos 
b   Centro de Investigación Lilly S.A., Avda. de la Industria 30, Alcobendas-Madrid 28108, Spain
,
Stellios Arseniyadis  ∗
a   Queen Mary University of London, School of Biological and Chemical Sciences, London, E1 4NS, UK
› Author AffiliationsEli Lilly and Queen Mary University of London are gratefully acknowledged for financial support.
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Dedicated to Professor K. C. Nicolaou on the occasion of his 74th birthday

Abstract

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.

Key words

acrylonitrile - surrogate - heterocycle - alkylation - Michael addition - palladium - retro-Dieckmann


Publication History

Received: 06 January 2021

Accepted after revision: 20 January 2021

Article published online:
01 February 2021

© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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