One-Pot Synthesis of Aryl Selenonic Acids and Some Unexpected Byproducts
| Autor: | Benjamin S. Gelfand, Kai N. Sands, Thomas G. Back |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Bromides
Ion exchange 010405 organic chemistry Metalation Aryl Organic Chemistry One-pot synthesis 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Selenious Acid Yield (chemistry) Organic chemistry Salts Hydrogen peroxide Oxidation-Reduction Derivative (chemistry) |
| Zdroj: | The Journal of Organic Chemistry. 86:9938-9944 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.1c01369 |
| Popis: | The synthesis of aryl selenonic acids was achieved from diverse aryl bromides via a one-pot method involving metalation, selenation, and oxidation with hydrogen peroxide followed by ion exchange to afford the pure products in 77-90% yield. An o-hydroxymethyl derivative was found to dehydrate readily, affording the first example of a cyclic selenonic ester, while two minor byproducts were isolated and shown by X-ray crystallography to be mixed salts of aryl selenonic acids with either the corresponding aryl seleninic or selenious acid. |
| Databáze: | OpenAIRE |
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