Gibson, SM;
D'Oyley, JM;
Higham, JI;
Sanders, K;
Laserna, V;
Aliev, AE;
Sheppard, TD;
(2018)
Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules.
European Journal of Organic Chemistry
, 2018
(29)
pp. 4018-4028.
10.1002/ejoc.201800668.
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Abstract
In this paper we outline how dihalohydration reactions of propargylic alcohols can be used to access a wide variety of useful halogenated building blocks. A novel procedure for dibromohydration of alkynes has been developed, and a selection of dichloro and dibromo diols and cyclic ethers were synthesized. The dihalohydration of homo‐propargylic alcohols provides a useful route to 3‐halofurans, which were shown to readily undergo cycloaddition reactions under mild conditions. Finally, a novel ring‐expansion of propargylic alcohols containing a cyclopropylalkyne provides access to halogenated alkenylcyclobutanes.
| Type: | Article |
|---|---|
| Title: | Dihalohydration of Alkynols: A Versatile Approach to Diverse Halogenated Molecules |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/ejoc.201800668 |
| Publisher version: | https://doi.org/10.1002/ejoc.201800668 |
| Language: | English |
| Additional information: | © 2018 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
| Keywords: | Halogenation, Alkynes, Alcohols, Heterocycles, Ketones |
| UCL classification: | UCL 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/10048589 |
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