Cooksey, JP, Kocieński, PJ and Blacker, AJ orcid.org/0000-0003-4898-2712 (2019) A Scalable Process for the Synthesis of 1,2-Dialkyldiselanes and 1-Alkaneselenols. Organic Process Research & Development, 23 (11). pp. 2571-2575. ISSN 1083-6160
Abstract
A four-step telescoped process for the synthesis of 1-alkaneselenols entails (1) the rapid formation of potassium selenocyanate from potassium cyanide and selenium in methanol, (2) the nucleophilic substitution of bromoalkanes or alkyl tosylates with potassium selenocyanate, (3) the mild base-catalyzed conversion of the resultant 1-alkaneselenocyanates to 1,2-dialkyldiselanes (the Krief reaction), and (4) the reduction of the resultant 1,2-dialkyldiselanes with hypophosphorous acid to give the desired 1-alkaneselenols. The process has been used to produce 1-octaneselenol on a 10.4 mol scale. Nine examples of the process are described.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2019 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Process Research and Development, copyright © American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.oprd.9b00380 |
Keywords: | alkylselenol; dialkyldiselenol; 1-octylselenol; potassium selenocyanate; reduced odor |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 30 Oct 2019 12:17 |
Last Modified: | 24 Oct 2020 00:39 |
Status: | Published |
Publisher: | American Chemical Society |
Identification Number: | 10.1021/acs.oprd.9b00380 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:152805 |