Substituent effects in the ring-chain tautomerism of 4-alkyl-2-aryl substituted oxazolidines and tetrahydro-1,3-oxazines

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

(Chemical Equation Presented) The condensation products of 2-aminoethanol or 3-aminopropanol (bearing an alkyl substituent on the carbon adjacent to the nitrogen) with substituted benzaldehydes proved to exist in CDCl3 at 300 K as three-component tautomeric mixtures of the diastereomeric five- or six-membered 1,3-O,N-heterocyclic ring forms and the corresponding imines. For each equilibrium, the electronic effects of the 2-aryl substituents were characterized by the Hammett equation. The steric effects of the alkyl groups could be described by Hansch-type equations for the equilibria involving oxazolidine ring forms. While the alkyl substituents did not cause any significant effect on the ring cis-chain and the ring trans-chain equilibria for tetrahydro-1,3-oxazines, increasing bulk of the 4-alkyl group increased the stability of the cyclic tautomers for the analogous oxazolidines.

Original languageEnglish
Pages (from-to)1465-1473
Number of pages9
JournalJournal of Heterocyclic Chemistry
Volume44
Issue number6
DOIs
Publication statusPublished - Jan 1 2007

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Substituent effects in the ring-chain tautomerism of 4-alkyl-2-aryl substituted oxazolidines and tetrahydro-1,3-oxazines'. Together they form a unique fingerprint.

  • Cite this