22.2. 5 Selenocarboxylic Acids and Derivatives (Update 2024)
Book
Editors: Campagne, J.-M. ; Donohoe, T. J.; Jiang, X. ; Wang, M.
Title: Knowledge Updates 2024/2
Online ISBN: 9783132457065; Book DOI: 10.1055/b000000968
1st edition © 2024 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
Selenocarboxylic acids and their derivatives are the selenium isologues of carboxylic, thioic, carbamic, and carbonic acids, and the corresponding esters, amides, and ureas, and are distinguished by the presence of a C=Se bond. The synthesis of these selenium analogues primarily involves incorporating selenium atoms into precursor molecules. This can be achieved by reducing elemental selenium to produce Se2– species, which are then introduced into electrophilic species. Alternatively, carbon nucleophiles can directly bond with elemental selenium, forming carbon–selenium bonds. Compounds containing a P=Se bond, such as Woollins’ reagent, are used to substitute the oxygen in a C=O bond with selenium, creating a C=Se bond. Carbon diselenide (CSe2) is another agent used in synthesizing these derivatives. However, extreme caution is required when handling CSe2 due to its potent odor and toxicity.
Key words
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