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Competitive kinetic study of the amination of organomagnesium and ‐zinc reagents with acetone O ‐sulfonyloxime
Author(s) -
Erdik Ender,
Ömür Özgen
Publication year - 2005
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.908
Subject(s) - chemistry , electrophilic amination , reagent , amination , electrophile , tetrahydrofuran , oxime , organic chemistry , acetone , substituent , medicinal chemistry , catalysis , solvent
Kinetic studies are reported for the electrophilic amination of substituted phenylmagnesium bromides and CuCN‐catalyzed 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.