Formation and characterization of a multicomponent equilibrium system derived from cis- and trans-1-aminomethylcyclohexane-1,2-diol

Anasztázia Hetényi, Zsolt Szakonyi, Karel D. Klika, Kalevi Pihlaja, Ferenc Fülöp

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19 Citations (Scopus)

Abstract

Both cis and trans isomers of amino diols 3-6 were prepared stereoselectively. In the reactions between 3-6 and phenyl isothiocyanate, the ring closure proceeded regioselectively and resulted only in spiro derivatives of 2-phenyliminooxazolidines 9, 10, 13, and 14. The reaction of cis-(or trans-)1-aminomethylcyclohexane-1,2-diol 4 (or 6) with 1 equiv of an aromatic aldehyde 15a-g in EtOH at room temperature resulted in a complex, multicomponent equilibrium mixture of 16a-g and 18a-g (or 17a-g and 19a-g), in each case consisting of a five-component, ring-chain tautomeric system 16A-E (or 17A-E), involving the Schiff base, two epimeric spirooxazolidines, two epimeric condensed 1,3-oxazines, and some of the four tricyclic compounds 18A-D (or 19A-D). The five-component, ring-chain equilibria were found to be adequately described by the Hammett-Brown linear free energy equation.

Original languageEnglish
Pages (from-to)2175-2182
Number of pages8
JournalJournal of Organic Chemistry
Volume68
Issue number6
DOIs
Publication statusPublished - Mar 21 2003

ASJC Scopus subject areas

  • Organic Chemistry

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