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Steric hindrance classified: treatment of isothiocyanatoallene with secondary amines bearing bulky substituents to generate 2-aminothiazoles†‡

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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Publication details

The article was received on 28 Feb 2019, accepted on 17 May 2019 and first published on 17 May 2019


Article type: Research Article
DOI: 10.1039/C9QO00312F
Org. Chem. Front., 2019, Accepted Manuscript

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    Steric hindrance classified: treatment of isothiocyanatoallene with secondary amines bearing bulky substituents to generate 2-aminothiazoles†‡

    K. Banert and J. Seifert, Org. Chem. Front., 2019, Accepted Manuscript , DOI: 10.1039/C9QO00312F

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