Substituent effects on the ring-chain tautomerism of 1,3-oxazines

F. Fülöp, L. Lázár, G. Bernáth, Reijo Sillanpää, Kalevi Pihlaja

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The aryl substituents at positions 4 and 6 do not exert observable electronic effects on the ring-chain tautomeric ratios of 2,4- or 2,6-diarylsubstituted-tetrahydro-1,3-oxazines. On the other hand, the electronic effect of the 2-aryl substituent is marked: in all eight series studied, the equilibria can be described by the equation log K = ρ{variant} σ+ +log K0, where ρ{variant}+ is the Hammett-Brown constant of the 2-aryl substituents, and ρ{variant} is a constant characteristic of the ring system (=0.75±0.05).

Original languageEnglish
Pages (from-to)2115-2122
Number of pages8
JournalTetrahedron
Volume49
Issue number10
DOIs
Publication statusPublished - Mar 5 1993

Fingerprint

Oxazines
oxazine 1

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Substituent effects on the ring-chain tautomerism of 1,3-oxazines. / Fülöp, F.; Lázár, L.; Bernáth, G.; Sillanpää, Reijo; Pihlaja, Kalevi.

In: Tetrahedron, Vol. 49, No. 10, 05.03.1993, p. 2115-2122.

Research output: Contribution to journalArticle

Fülöp, F. ; Lázár, L. ; Bernáth, G. ; Sillanpää, Reijo ; Pihlaja, Kalevi. / Substituent effects on the ring-chain tautomerism of 1,3-oxazines. In: Tetrahedron. 1993 ; Vol. 49, No. 10. pp. 2115-2122.
@article{c214ef11c28a452b9e43c9f2329ba367,
title = "Substituent effects on the ring-chain tautomerism of 1,3-oxazines",
abstract = "The aryl substituents at positions 4 and 6 do not exert observable electronic effects on the ring-chain tautomeric ratios of 2,4- or 2,6-diarylsubstituted-tetrahydro-1,3-oxazines. On the other hand, the electronic effect of the 2-aryl substituent is marked: in all eight series studied, the equilibria can be described by the equation log K = ρ{variant} σ+ +log K0, where ρ{variant}+ is the Hammett-Brown constant of the 2-aryl substituents, and ρ{variant} is a constant characteristic of the ring system (=0.75±0.05).",
author = "F. F{\"u}l{\"o}p and L. L{\'a}z{\'a}r and G. Bern{\'a}th and Reijo Sillanp{\"a}{\"a} and Kalevi Pihlaja",
year = "1993",
month = "3",
day = "5",
doi = "10.1016/S0040-4020(01)86311-0",
language = "English",
volume = "49",
pages = "2115--2122",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "10",

}

TY - JOUR

T1 - Substituent effects on the ring-chain tautomerism of 1,3-oxazines

AU - Fülöp, F.

AU - Lázár, L.

AU - Bernáth, G.

AU - Sillanpää, Reijo

AU - Pihlaja, Kalevi

PY - 1993/3/5

Y1 - 1993/3/5

N2 - The aryl substituents at positions 4 and 6 do not exert observable electronic effects on the ring-chain tautomeric ratios of 2,4- or 2,6-diarylsubstituted-tetrahydro-1,3-oxazines. On the other hand, the electronic effect of the 2-aryl substituent is marked: in all eight series studied, the equilibria can be described by the equation log K = ρ{variant} σ+ +log K0, where ρ{variant}+ is the Hammett-Brown constant of the 2-aryl substituents, and ρ{variant} is a constant characteristic of the ring system (=0.75±0.05).

AB - The aryl substituents at positions 4 and 6 do not exert observable electronic effects on the ring-chain tautomeric ratios of 2,4- or 2,6-diarylsubstituted-tetrahydro-1,3-oxazines. On the other hand, the electronic effect of the 2-aryl substituent is marked: in all eight series studied, the equilibria can be described by the equation log K = ρ{variant} σ+ +log K0, where ρ{variant}+ is the Hammett-Brown constant of the 2-aryl substituents, and ρ{variant} is a constant characteristic of the ring system (=0.75±0.05).

UR - http://www.scopus.com/inward/record.url?scp=0027413294&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027413294&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)86311-0

DO - 10.1016/S0040-4020(01)86311-0

M3 - Article

AN - SCOPUS:0027413294

VL - 49

SP - 2115

EP - 2122

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 10

ER -