Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Syntheses of N-Vinylphthalimide Derivatives
Kiyoshi KATO
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1960 Volume 18 Issue 5 Pages 343-346

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Abstract
Reaction of N-(1-chloroethyl) phthalimidej and thioglycolic acid at room temperature caused dehydrochlorination and gave N-(1-carboxymethylmercaptoethy1) phthalimide with good yield. This substance can be esterified easily with alcohols in the presence of sulfuric acid as a catalyst.
An addition reaction of thioglycolic acid to N-vinylphthalimide in the presence of sulfuric acid catalyst was followed by Markownikoff's rule and formed an α-addition product, N-(1-carboxymethylmercaptoethyl) phthalimide. Similarly, methyl and ethyl thioglycolate gave additive products.
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© The Society of Syhthetic Organic Chemistry, Japan
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