Ring—Chain Tautomerism in 1,3-Oxazines

Ferenc Fülö, Kalevi Pihlaja, Jorma Mattinen, Gabor Bernath

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Abstract

A comparative study on the ring-chain tautomerism of 49 2-(substituted-phenyl) tetrahydro-l,3-oxazines of seven different types, namely, tetrahydro-1,3-oxazines 3, r-8a,c-2,c-4a- and r-8a,c-2, t-4a-1,3-perhydrobenzoxazines 5 and 7, r-8a,c-2,c-4- and r-8a,c-2,t-4a-l,3-perhydrobenzoxazines 9 and 11, 3,4-dihydro-2H-l,3-benzoxazines 12, and l,2-dihydro-4H-3,l-benzoxazines 13, pointed out that in all cases the equilibria can be described with a simple equation, log Kx= (0.76 ± 0.04)σ++ log Xx= Hwhere Kx= [ring]/[chain] (X = H). A factor c illustrating the sum of steric and electronic effects of substituents at C-4, C-5, and C-6 has also been introduced.

Original languageEnglish
Pages (from-to)3821-3825
Number of pages5
JournalJournal of Organic Chemistry
Volume52
Issue number17
DOIs
Publication statusPublished - Aug 1 1987

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ASJC Scopus subject areas

  • Organic Chemistry

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