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DOI: 10.1055/s-0040-1706019
4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent
Eli Lilly and Queen Mary University of London are gratefully acknowledged for financial support.
![](https://www.thieme-connect.de/media/10.1055-s-00032269/202101/lookinside/thumbnails/so-2021-d0002-r_10-1055_s-0040-1706019-1.jpg)
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-DieckmannPublication History
Received: 06 January 2021
Accepted after revision: 20 January 2021
Article published online:
01 February 2021
© 2021. The Author(s). 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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