Aminolyses of 4-nitrophenyl phenyl carbonate and thionocarbonate: effect of modification of electrophilic center from C=O to C=S on reactivity and mechanism.

@article{Um2006AminolysesO4,
  title={Aminolyses of 4-nitrophenyl phenyl carbonate and thionocarbonate: effect of modification of electrophilic center from C=O to C=S on reactivity and mechanism.},
  author={I. Um and E. Kim and Hye-Ran Park and Sangeun Jeon},
  journal={The Journal of organic chemistry},
  year={2006},
  volume={71 6},
  pages={
          2302-6
        }
}
  • I. Um, E. Kim, +1 author Sangeun Jeon
  • Published 2006
  • Chemistry, Medicine
  • The Journal of organic chemistry
  • 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 proposed to proceed through a stepwise mechanism with a change… CONTINUE READING
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