The Journal of Organic Chemistry

Phosphoric amides. 5. Acid-catalyzed hydrolysis of dimethyl N-(alkylphenyl) phosphoramidates

TA Modro, BP Rijkmans

Index: Modro, Tomasz A.; Rijkmans, Bloys P. Journal of Organic Chemistry, 1982 , vol. 47, # 17 p. 3208 - 3211

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Citation Number: 10

Abstract

Studies of the acid-catalyzed hydrolysis of dimethyl N-(alkylpheny1) phosphroamidates demonstrate that the LFER between observed rates and basicities of the leaving amines is different for meta/para-and for orthosubstituted derivatives (slopes of log how vs. pK, are 0.4 and 0.9, respectively). Since the AS* values and KSIE determined are approximately constant irrespective of the position of an alkyl group, the observed change in the slope of ...