Reaction of Acetoacetanilide with Trimethylchlorosilane

Acetoacetanilide reacts with trimethylchlorosilane (reagent ratio 1:1) in a hexane medium at room temperature to form N -phenyl-3-[(trimethylsilyl)oxy]but-2-enamide as a mixture of E and Z isomers in the ratio 11 : 0.1. Multinuclear NMR monitoring showed that at room temperature the ratio of isomers...

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Bibliographic Details
Published in:Russian journal of general chemistry 2023-11, Vol.93 (Suppl 1), p.S203-S209
Main Authors: Lazareva, N. F., Albanov, A. I., Lazarev, I. M., Soldatenko, A. S.
Format: Article
Language:English
Subjects:
Acetoacetanilides
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Hexanes
Isomerization
Isomers
NMR
Nuclear magnetic resonance
Reagents
Room temperature
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Summary:Acetoacetanilide reacts with trimethylchlorosilane (reagent ratio 1:1) in a hexane medium at room temperature to form N -phenyl-3-[(trimethylsilyl)oxy]but-2-enamide as a mixture of E and Z isomers in the ratio 11 : 0.1. Multinuclear NMR monitoring showed that at room temperature the ratio of isomers E : Z gradually changes in a CDCl 3 solution, reaching 3.1 : 9.6 after 14 days. A possible mechanism of the isomerization is discussed.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363223140049