TY  - JOUR
AU  - Hetényi, Anasztázia
AU  - Szakonyi, Zsolt
AU  - Klika, K D
AU  - Pihlaja, K
AU  - Fülöp, Ferenc
TI  - Formation and characterization of a multicomponent equilibrium system derived from cis- and trans-1-aminomethylcyclohexane-1,2-diol
JF  - JOURNAL OF ORGANIC CHEMISTRY
J2  - J ORG CHEM
VL  - 68
PY  - 2003
IS  - 6
SP  - 2175
EP  - 2182
PG  - 8
SN  - 0022-3263
DO  - 10.1021/jo026428t
UR  - https://m2.mtmt.hu/api/publication/1013533
ID  - 1013533
N1  - CAplus AN 2003:127465; MEDLINE PMID: 12636377 (Journal; Article);
AB  - 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.
LA  - English
DB  - MTMT
ER  -