Aminolyses of 4-Nitrophenyl Phenyl Carbonate and Thionocarbonate: Effect of Modification of Electrophilic Center from CO to CS on Reactivity and Mechanism

IH Um, EY Kim, HR Park, SE Jeon

Index: Um, Ik-Hwan; Kim, Eun Young; Park, Hye-Ran; Jeon, Sang-Eun Journal of Organic Chemistry, 2006 , vol. 71, # 6 p. 2302 - 2306

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Citation Number: 65

Abstract

A kinetic study is reported for nucleophilic substitution reactions of 4-nitrophenyl phenyl carbonate (5) and 4-nitrophenyl phenyl thionocarbonate (6) with a series of primary amines. The thiono compound 6 is less reactive than its oxygen analogue 5 toward strongly basic amines but is more reactive toward weakly basic CF3CH2NH2. The Brønsted-type plots obtained from the aminolyses of 5 and 6 are curved downwardly. The reactions are ...

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