%X The condensation of Betti base analog aminonaphthols with substituted benzaldehydes or aliph. aldehydes led to 1,3-diaryl-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines (16-22) and 3-alkyl-1-aryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines (23-29), which proved to be three-component (r1-o-r2, 16-22) or two-component (r1-r2, 23-29) tautomeric mixts. in CDCl3 at 300 K. The electronic effects of the 3-aryl or 3-alkyl groups on the tautomeric ratios could be described by the equation log KX = ρσ+ + log KX=H (16-22) and log KR = 7.88Va + 0.55 (23-29) resp. Study of the influence of aryl substituents at position 1 indicated that in the trans form a stereoelectronic effect is present; this was supported by dual substituent parameter treatment of the 13C chem. shift changes induced by Ph substituents. [on SciFinder(R)]
%J ANNALS OF WEST UNIVERSITY OF TIMISOARA-SERIES CHEMISTRY
%P 175-182
%A  SzatmĂĄri IstvĂĄn
%A  Martinek TamĂĄs
%A  LĂĄzĂĄr LĂĄszlĂł
%A  Koch Andreas
%A  Kleinpeter Erich
%A  FĂźlĂśp Ferenc
%N 3
%R MTMT:3258704
%D 2003
%O N1 CAPLUS AN 2004:762070(Journal)
%I szte
%T Substituent effects in the ring-chain tautomerism of 1-aryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines
%V 12
%L publicatio30979