ChemInform Abstract: Decarboxylative Elimination of Enol Triflates as a General Synthesis of Acetylenes

Autor:	Chandrashekar Ramarao, Ian Fleming
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Potassium carbonate Elimination reaction chemistry.chemical_compound Hydrolysis Chemistry Decarboxylation Carboxylic acid Trifluoroacetic acid General Medicine Medicinal chemistry Enol Alkyl
Zdroj:	ChemInform. 30
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.199937062
Popis:	The enol trifluoromethanesulfonates 4, 8, 12, 17 and 20 of tert-butyl β-ketodiesters and β-ketoesters can be hydrolysed to the corresponding carboxylic acids by dissolution in trifluoroacetic acid. The dicarboxylic acids undergo mild decarboxylative elimination to give the acetylenic acids 4 and 9 in aqueous sodium bicarbonate solution at room temperature. Similarly, the monocarboxylic acids give the terminal and mid-chain acetylenes 13, 18, 21 and 24 by refluxing in acetone with potassium carbonate. One of the substituents on the acetylenes can be methyl, primary alkyl, secondary alkyl or ethynyl, and the other can be a carboxylic acid, hydrogen or primary alkyl, but the enol trifluoromethanesulfonates could not be prepared when one of the substituents was tert-butyl, nor when both substituents on the precursor to the acetylene were secondary alkyl.
Databáze:	OpenAIRE
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