Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Condensation of the Triad System with Carbonyl Compounds. I. Condensation of Ethyl Itaconate with Ketones
Chiaki KatsutaNoboru Sugiyama
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1962 Volume 35 Issue 7 Pages 1194-1199

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Abstract

In the presence of sodium ethoxide, ethyl itaconate condensed with ketones (acetone and cyclohexanone) at the terminal carbon atoms of its triad system without any appreciable isomerisation and afforded novel compounds, α-methyl-γ,γ-disubstituted aconic acids (C) and α-alkylidenemethyl-γ,γ-disubstituted aconic acids (D).
(Remark: Graphics omitted.)
The chemical structures of C and D were determined by ultraviolet, infrared, NMR spectra etc.
A reaction mechanism has been proposed (p. 1197).

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