![Methyl 2-[5-(3-Phenoxyphenyl)-2H-tetrazol-2-yl]acetate structure](https://static.chemtradehub.com/structs/130/1305320-60-8-84b4.webp "Methyl 2-[5-(3-Phenoxyphenyl)-2H-tetrazol-2-yl]acetate structure")
Methyl 2-[5-(3-Phenoxyphenyl)-2H-tetrazol-2-yl]acetate
CAS Number:
1305320-60-8
Molecular Formula:
C16H14N4O3
Steric hindrance classified: treatment of isothiocyanatoallene with secondary amines bearing bulky substituents to generate 2-aminothiazoles‡
Literature Information
Publication Date
2019-05-17
DOI
10.1039/C9QO00312F
Impact Factor
5.281
Authors
Klaus Banert, Jennifer Seifert
View Original
Abstract
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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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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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Molecular Formula:
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