Tetrahedron

Influence des substituants sur la tautomerie cycle-chaine en serie hydroxy-5 isoxazoline-2

R Escale, R Jacquier, B Ly, F Petrus, J Verducci

Index: Escale,R. et al. Tetrahedron, 1976 , vol. 32, p. 1369 - 1373

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Citation Number: 18

Abstract

The ring-chain tautomerism of 5-hydroxy-2-isoxazolines has been investigated. By increasing bulk and/or number of substituents, the ring tautomer is generally favoured due to conformational factors in the chain tautomer. Introduction of two methyl groups at position 4 produces an exaltation of this effect (gem-dimethyl effect). The 5-substituent has also a steric and electronic influence on the reactivity of the chain carbonyl group.