Kinetic study of the amination of Grignard reagents and cuprates with <i>O</i>-methylhydroxylamine

Erdik E., Eroglu F., KAHYA N. D.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, no.9, pp.950-956, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2005
  • Doi Number: 10.1002/poc.933
  • Journal Name: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.950-956
  • Keywords: Grignard reagents, magnesium cuprates, zinc cyanocuprates, electrophilic animation, O-methylhydroxylamine, competitive kinetics, Hammett plots, ELECTROPHILIC AMINATION, ORGANOLITHIUM REAGENTS, AB-INITIO, MECHANISM, ORDER, DISPLACEMENTS, BENZOPHENONE, REACTIVITY, GEOMETRY, MODEL
  • Ankara University Affiliated: Yes

Abstract

Substituent effects on the rate of electrophilic amination of phenylmagnesiurn bromides, magnesium dipherylcuprates and catalytic phenylzinc cyanocuprates with O-methyhydroxylamine in THF were investigated in a competitive kinetic study. Rate data and Hammett substituent constants are discussed on the basis of proposed mechanisms for the substitution reactions of these organometallics with an electrophilic amino transfer reagent. Copyright (c) 2005 John Wiley & Sons, Ltd.