Synthèse et étude du réarrangementdes diazoles-1,3: alkyl-1 alkylthio-2 (allylthio, arylthio, cycloalkylthio) imidazoles. Partie II. Réarrangement et réactions parasites
作者:
Jacky Kister,
Georges Assef,
Gilbert Mille,
Jacques Metzger,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1979)
卷期:
Volume 57,
issue 7
页码: 822-830
ISSN:0008-4042
年代: 1979
DOI:10.1139/v79-135
出版商: NRC Research Press
数据来源: NRC
摘要:
The kinetics of therearrangement reaction for a series of 1-alkyl-2-alkylthio (or allylthio, arylthio, cycloalkylthio) imidazoles has been studied at various temperatures. The rearrangement and hydrolysis results have been compared with those of 1-alkyl-2-methylthio-Δ-2-imidazolines and 1-alkyl-2-methylthio-Δ-2-tetrahydropyrimidines. Electronic and steric effects are discussed and a parallel between pKaand rearrangement is proposed. The limit of this parallel is either a structural effect such as direct (orthoeffect) or indirect (cycle deformation) steric interactions or geometric modifications of the heterocycles studied (five- or six-membered cycles). All these results permitted the coherent choice of the amplification compound of a nonconventional photographic process.
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