ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
α-Amino Acids as Nucleophilic Acyl Equivalents, IV. Synthesis of Symmetrical Ketones by Means of 2-Phenyl-2-oxazolin-5-one2-Phenyl-2-oxazolin-5-one (2), itself easily derivable from hippuric acid (1), on reaction with allyl, benzyl or phenacyl halides undergoes 4,4-disubstitution, if the reaction is conducted in dipolar aprotic solvents in presence of weak bases. Hydrolysis of the resulting oxazolinones 3 leads to α, α-dialkylated hippuric acids 4, which may be oxidized to symmetrical ketones 5 by means of lead tetraacetate.
Notes:
Das aus Hippursäure (1) leicht zugängliche 2-Phenyl-2-oxazolin-5-on (2) wird von Allyl-, Benzyl-oder Phenacylhalogeniden in 4-Stellung doppelt substituiert, wenn die Reaktion in dipolar aprotischen Lösungsmitteln in Gegenwart schwacher Basen durchgeführt wird. Hydrolyse der erhaltenen Oxazolinone 3 liefert α, α-disubstituierte Hippursäuren 4, die mit Bleitetraacetat zu symmetrischen Ketonen 5 oxidiert werden.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19801131204
