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Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study.

ABSTRACT: Treatment of alkoxy-substituted o-(pivaloylaminomethyl)benzaldehydes under acidic conditions resulted in the formation of the regioisomeric aldehydes and/or dimer-like products. Detailed NMR studies and single-crystal X-ray measurements supported the structure elucidation of the compounds. DFT calculations were also carried out to clarify the reaction mechanism, and to explain the observed product distributions and structural variances in the dimer-like products. Studies on the transformation of unsubstituted o-(pivaloylaminomethyl)benzaldehyde under similar conditions were presented as well.

SUBMITTER: Hargitai C

PROVIDER: S-EPMC7372232 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study.

Hargitai Csilla C Koványi-Lax Györgyi G Nagy Tamás T Ábrányi-Balogh Péter P Dancsó András A Tóth Gábor G Halász Judit J Pandur Angéla A Simig Gyula G Volk Balázs B

Beilstein journal of organic chemistry 20200713

Treatment of alkoxy-substituted o-(pivaloylaminomethyl)benzaldehydes under acidic conditions resulted in the formation of the regioisomeric aldehydes and/or dimer-like products. Detailed NMR studies and single-crystal X-ray measurements supported the structure elucidation of the compounds. DFT calculations were also carried out to clarify the reaction mechanism, and to explain the observed product distributions and structural variances in the dimer-like products. Studies on the transforma ...[more]

PMID: 32733608

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