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Ring-chain tautomerism and three- to four-component equilibria in fused-ring tetrahydro-1,3-oxazines

✍ Scribed by Kalevi Pihiaja; Aija Parkkinen; Ferenc Fülöp; Jonna Mattinen; Gábor Bernath

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
489 KB
Volume
47
Category
Article
ISSN
0040-4020

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✦ Synopsis

The condensation of &-(1) and trans-2-hydroxymethyl-4-cyclohexenvl-l-amine (21 and 2,3-w-

(3) cyclo?2.2.l]heptyl&nine (4j and 2,3-d.&&-3_hydroxymethylbiwith 8 -different-aromatic aldehydes led to ring-chain tautomeric equilibria between epimeric tetrahydro-1,3-oxazines and open-chain Schiff bases. In all cases the equilibrium mixtures consisted of two epimeric ring forms although the 2-axial epimers of the cyclohexene-fused derivatives had only a minor contribution to the ringchain tautomeric equilibria. For the norbornane-fused derivatives the ring-chain tautomeric equilibria were taken equal to the ratio of the sum of the ring forms and the amount of the $-isomer of the open form in which case the simple equation, log KK = 0.76~ + log K derived recently for ring-chain tautomerism in 1,3-oxazines prevailes=ffgain for each system studied.

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