Studies on Geometrical Isomerism by Nulear Magnetic Resonance. V. Stereochemistry of 5-Substituted 4-Alkoxycarbonyl-2-carbamoylimino-1,3-oxathiolanes
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概要
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An equimolar reaction of thiocyanoacetic esters with aldehydes in the presence of potassium fluoride or carbonate leads to a stereoisomeric mixture of <I>cis</I> and <I>trans</I> isomers of 5-substituted 4-alkoxycarbonyl-2-carbamoylimino1,3-oxathiolanes. Several of them were separated into two isomeric forms, whose geometrical configurations were determined by means of nuclear magnetic resonance technique. The vicinal coupling constant between the 4-and 5-protons is consistently larger for the <I>cis</I> forms than for the <I>trans</I>. In the case of the 5-aryl derivatives, the signals of the alkoxycarbonyl group appear at higher field for the <I>cis</I> isomers than for the <I>trans</I>. The composition ratios of <I>cis</I> and <I>trans</I> isomers of the oxathiolanes prepared are determined. Infrared data of the <I>cis</I> and <I>trans</I> oxathiolanes are also reported.
- 公益社団法人 日本化学会の論文
著者
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UZAWA Jun
The Institute of Physical and Chemical Research
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Yokono Tetsuro
The Institute of Physical and Chemical Research
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Akano Makiko
The Institute of Physical and Chemical Research
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Midorikawa Hiroshi
The Institute of Physical and Chemical Research
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Hayashi Toshio
The Institute of Physical and Chemical Research
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Kambe Satoshi
The Institute of Physical and Chemical Research
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