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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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