22.2. 5 Selenocarboxylic Acids and Derivatives (Update 2024)
Buch
Herausgeber: Campagne, J.-M. ; Donohoe, T. J.; Jiang, X. ; Wang, M.
Titel: Knowledge Updates 2024/2
Online ISBN: 9783132457065; Buch-DOI: 10.1055/b000000968
1st edition © 2024 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
Science of Synthesis Knowledge Updates
Übergeordnete Publikation
Titel: Science of Synthesis
DOI: 10.1055/b-00000101
Reihenherausgeber: 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.
Typ: Mehrbändiges Werk
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.
Schlüsselwörter
selenocarboxylic acids - selenocarboxylic acid O-esters - selenocarboxylic acid amides (selenoamides), selenocarbonates, - selenothiocarboxylic acids - diselenocarboxylic acids - selenothioic acid S-esters - selenocarbamate O-esters - selenoureas - diselenocarbonates - diselenocarbamates - diselenothiocabonates - triselenocarbonates - Woollin’s reagent - elemental selenium - carbon diselenide - 2-selenazolines - four-component coupling reactions- 3 Gómez Castaño JA, Romano RM, Beckers H, Willner H, Boese R, Della Védova CO. Angew. Chem. Int. Ed. 2008; 47: 10 114
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