Competitive kinetic study of the amination of organomagnesium and -zinc reagents with acetone O-sulfonyloxime

Erdik E., Omur Ö.

Applied Organometallic Chemistry, cilt.19, sa.7, ss.887-893, 2005 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 19 Sayı: 7
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1002/aoc.908
  • Dergi Adı: Applied Organometallic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.887-893
  • Anahtar Kelimeler: Grignard reagents, zinc cyanocuprates, electrophilic amination, competitive kinetics, O-(arenesulfonyl)ketoximes, Hammett plots, ELECTROPHILIC AMINATION, PRIMARY AMINES, GRIGNARD-REAGENTS, ORGANOLITHIUM REAGENTS, BENZOPHENONE, ORDER, DISPLACEMENTS, DERIVATIVES, REACTIVITY, ALKYLATION
  • Ankara Üniversitesi Adresli: Evet

Özet

Kinetic studies are reported for the electrophilic amination of substituted phenylmagnesium bromides and CuCN-cataly/ed phenylzinc chlorides with acetone O-(2,4,6-trimethylphenylsulfonyl)oxime in tetrahydrofuran at reflux temperature and at room temperature respectively. Substituent effects were determined by competition experiments. Rate data are analyzed via Hammett relationships to support the proposed mechanisms for the substitution of these organometallics with an electrophilic amino transfer reagent. Copyright © 2005 John Wiley & Sons, Ltd.