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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.
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-DieckmannPublikationsverlauf
Eingereicht: 06. Januar 2021
Angenommen nach Revision: 20. Januar 2021
Artikel online veröffentlicht:
01. Februar 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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