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Transition-metal-free synthesis of ynol ethers and thioynol ethers via displacement at sp centers: a revised mechanistic pathway

Gray, VJ; Cuthbertson, J; Wilden, JD; (2014) Transition-metal-free synthesis of ynol ethers and thioynol ethers via displacement at sp centers: a revised mechanistic pathway. The Journal of Organic Chemistry , 79 (12) pp. 5869-5874. 10.1021/jo500814y. Green open access

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Abstract

We present here valuable extensions to our previous work in preparing highly functionalized, heteroatom-substituted alkynes via displacement at an sp center. Our results show that a wide range of ynol ethers can be prepared by the same methodology and that the same protocol can be applied to the synthesis of synthetically useful thioynol ethers. We also present new observations that have led us to revise our original hypothesis in favor of a pathway involving radical intermediates.

Type: Article
Title: Transition-metal-free synthesis of ynol ethers and thioynol ethers via displacement at sp centers: a revised mechanistic pathway
Location: United States
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/jo500814y
Publisher version: http://dx.doi.org/10.1021/jo500814y
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1474727
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