Proton magnetic resonance studies of cis-trans equilibria of some N-(2,5-dichlorophenyl)-3-aminocrotonamides.
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The <SUP>1</SUP>H NMR spectra of 3-(alkylamino)crotonamides indicate that these substances exist in solution as a mixture of the geometric isomers, <I>cis</I> and <I>trans</I>, in which the chelated <I>cis</I> form is predominant. Unsubstituted 3-aminocrotonamide appears to exist in the <I>cis</I> form only, and <I>N</I>,<I>N</I>-disubstituted derivatives in the <I>trans</I> form. In the case of 3-(alkylamino)crotonamide it is found that the <I>cis</I>-<I>trans</I> equilibrium is solvent dependent and that the apparent rate of interconversion between the isomers is very slow in chloroform-<I>d</I>, fast in dimethyl-<I>d</I><SUB>6</SUB> sulfoxide, and intermediate in acetone-<I>d</I><SUB>6</SUB> and methanol-<I>d</I><SUB>4</SUB>. It seems that the <I>cis</I>-<I>trans</I> equilibrium is almost independent of both temperature and concentration, and that the replacement of the olefinic H by D proceeds through enamine\rightleftharpoonsimine tautomerization.
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