Highly efficient intramolecular nucleophilic reactions. Cyclization of p-nitrophenyl N-(2-mercaptophenyl)-N-methylcarbamate and phenyl N-(2-aminophenyl)-N- …

TH Fife, JEC Hutchins, MS Wang

文献索引：Fife,T.H. et al. Journal of the American Chemical Society, 1975 , vol. 97, p. 5878 - 5882

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被引用次数: 32

摘要

Abstract: p-Nitrophenyl N-(2-mercaptophenyl)-N-methylcarbamate cyclizes rapidly at 25'to N- methylbenzothiazolone with release of p-nitrophenol. The pH-rate constant profile is sigmoidal with pK,,,= 8.7. The effective molarity of the neighboring sulfhydryl group is 1.4 X los M in comparison with bimolecular attack of thiols on p-nitrophenyl N-methyl-N- phenylcarbamate. The pH-rate constant profile for cyclization of phenyl N-(2-aminophenyl) ...