Chemistry of Heterocyclic Compounds p. 693 - 696 (1982)
Update date:2022-09-26
Topics:
Solov'eva, N. P.
Marchenko, N. B.
Granik, V. G.
Sheinker, Yu. N.
A number of secondary enamines and cyclic enol ethers (2-methylenetetrahydrofuran derivatives) were synthesized by the reaction of O-methylbutyrolactim and 2,2-diethoxytetrahydrofuran, respectively, with compounds that have an active methylene link.The absence of reversible cis-trans isomerization was established in a study of the PMR spectra of these compounds.The configuration of the secondary enamines is determined by the possibility of the formation of a strong intramolecular hydrogen bond between the carbonyl-containing substituent and the NH group.In the case of the cyclic enol ethers it was shown that the energy barrier to cis-trans isomerization is greater than 25 kcal/mole and that, as a consequence of this, the geometrical isomers can be separated preparatively.
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Doi:10.1055/s-1982-29944
(1982)Doi:10.1021/ja00388a073
(1982)Doi:10.1246/cl.1988.261
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(2014)Doi:10.1016/0040-4020(82)80085-9
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(2005)
