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Stereochemistry in the reaction of alkylsulfinyl phenylmethyl carbanion with electrophiles

✍ Scribed by Masato Higaki; Mutsuo Goto; Atsuyoshi Ohno

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
413 KB
Volume
1
Category
Article
ISSN
1042-7163

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✦ Synopsis

Stereochemistry of the reactions of methyl-, ethyl-, 2propyl-, and 1 ,I -dimethylethylsulfinyl phenylmethyl carbanions with deuterium oxide and methyl iodide in tetrahydro furan have been studied. The 2-propylsulfinyl phenylmethyl carbanion exerts abnormal behavior in the sense that the alkyl substituent herein has no ability to freeze the conformation of the carbanion. The results are interpreted i n terms of hard and soft interactions. 'Li and "0 nuclear magnetic resonance ( N M R ) spectroscopy revealed that the carbanions derived from these sulfoxides behave as the oxylate form.

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