Stereoelectronic effects in ring-chain tautomerism of 1, 3-diarylnaphth [1, 2-e][1, 3] oxazines and 3-alkyl-1-arylnaphth [1, 2-e][1, 3] oxazines

…, E Kleinpeter, K Neuvonen, F Fülöp

Index: Szatmari, Istvan; Martinek, Tamas A.; Lazar, Laszlo; Koch, Andreas; Kleinpeter, Erich; Neuvonen, Kari; Fueloep, Ferenc Journal of Organic Chemistry, 2004 , vol. 69, # 11 p. 3645 - 3653

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Citation Number: 60

Abstract

The disubstitution effects of X and Y in 1-(Y-phenyl)-3-(X-phenyl)-2, 3-dihydro-1 H-naphth [1, 2-e][1, 3] oxazines on the ring-chain tautomerism, the delocalization of the nitrogen lone pair (anomeric effect), and the 13C NMR chemical shifts were analyzed by using multiple linear regression analysis. Study of the three-component equilibrium B⇌ A⇌ C revealed that the chain⇌ trans (A⇌ B) equilibrium constants are significantly influenced by the inductive ...