Grounds, H;
Ermanis, K;
Newgas, SA;
Porter, MJ;
(2017)
Conversion of Alcohols to Phosphorothiolates Using a Thioiminium Salt as Coupling Agent.
Journal of Organic Chemistry
, 82
(23)
pp. 12735-12739.
10.1021/acs.joc.7b01657.
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Abstract
We report a method for the direct and rapid conversion of primary and secondary alcohols to the corresponding phosphorothiolates in yields ranging from 64% to 97%, using as a coupling agent the iminium salt prepared from N,N-dimethylthioformamide and Meerwein’s salt. Selective reaction of primary alcohols in the presence of secondary alcohols is possible. The reaction of secondary alcohols proceeds stereospecifically with inversion of configuration.
Type: | Article |
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Title: | Conversion of Alcohols to Phosphorothiolates Using a Thioiminium Salt as Coupling Agent |
Open access status: | An open access version is available from UCL Discovery |
DOI: | 10.1021/acs.joc.7b01657 |
Publisher version: | https://doi.org/10.1021/acs.joc.7b01657 |
Language: | English |
Additional information: | This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
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/10027743 |
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