Steric hindrance classified: treatment of isothiocyanatoallene with secondary amines bearing bulky substituents to generate 2-aminothiazoles‡
文献信息
发布日期
2019-05-17
DOI
10.1039/C9QO00312F
影响因子
5.281
作者
Klaus Banert, Jennifer Seifert
查看原文
摘要
Twenty secondary amines, bearing two secondary, two tertiary, or a secondary and a tertiary alkyl group or a neopentyl group, were treated with allenyl isothiocyanate to prepare the corresponding 2-dialkylamino-5-methylthiazoles. The relative rates of these reactions, which were strongly dependent on the steric demand of the N-alkyl groups, were measured by using competition experiments and analysis by 1H NMR spectroscopy. Not only steric, but also some electronic effects on the nucleophilicity of the dialkylamines were discussed.
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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