Intermediates in the reaction of aniline with formaldehyde catalyzed by acids

Research output: Contribution to journalArticle

Abstract

The relative stabilities and reactivities of possible intermediates in the reaction of aniline with formaldehyde under conditions of acid catalysis were estimated by the semiempirical MNDO method. According to the calculation results, protonated N-(hydroxymethyl)aniline and ortho-, meta-, and paraσ-complexes are formed through the ion-dipole complex. Further transformations of these intermediates, which determine the structure of the final products, depend on the possibility of proton abstraction from the σ-complexes with formation of a quinonimine structure, as well as on the lability of the hydroxymethyl group in the protonated amino alcohol.

Original languageEnglish
Pages (from-to)679-683
Number of pages5
JournalRussian Journal of Organic Chemistry
Volume36
Issue number5
Publication statusPublished - 1 May 2000

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Formaldehyde
Amino Alcohols
Acids
Catalysis
Protons
Ions
aniline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Intermediates in the reaction of aniline with formaldehyde catalyzed by acids. / Bochkarev, V. V.; Soroka, L. S.

In: Russian Journal of Organic Chemistry, Vol. 36, No. 5, 01.05.2000, p. 679-683.

Research output: Contribution to journalArticle

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