Tautomerization tendencies of 2-acetylcycloalkanones, 2-acetyl-1,3-cycloalkanediones, and cyclic β-keto esters of five- and six-membered rings

被引：0

作者：

Rojas, A. ^{[1
]}

Perez-Encabo, A. ^{[1
]}

Herraiz-Sierra, I. ^{[1
]}

Blanco, C.A. ^{[1
]}

机构：

[1] Depto. Ingenieria Agric., E.T.S. Ingeniarias Agrarias, Universidad de Valladolid, 34071 Palencia, Spain

来源：

Canadian Journal of Chemistry | 2001年 / 79卷 / 04期

关键词：

Esters - Ionization - Ketones - Nuclear magnetic resonance spectroscopy - Solutions;

D O I：

10.1139/v01-061

中图分类号：

学科分类号：

摘要：

NMR and kinetics studies of the tautomeric equilibrium of 2-acetylcycloalkanones, 2-acetyl-1,3-cycloalkanediones, and methyl 2-oxocycloalkanecarboxylates of five- and six-membered rings have been carried out. By comparing 1H NMR and 13C NMR spectra recorded in D2O-DOCD3 and CDCl3, with those results derived using a bromination kinetic procedure in dilute aqueous solution, information concerning tautomeric interconversion is provided. Some discussions considering ionisation equilibria and rate constants involved have also been considered. Solvent and concentration effects on keto-enol equilibria have also been discussed.

引用

页码：448 / 454

共 14 条

[1] Tautomerization tendencies of 2-acetylcycloalkanones, 2-acetyl-1,3-cycloalkanediones, and cyclic β-keto esters of five- and six-membered rings.
Rojas, A
Perez-Encabo, A
Herraiz-Sierra, I
Blanco, CA
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (04): : 448 - 454
[2] Group 13 five- and six-membered rings with rare 2π aromaticity
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[3] CONDENSATION OF 2-ACETYL-1,3-CYCLOALKANEDIONES WITH DIALKYLACETALS OF N,N-DIALKYLFORMAMIDES AS A SIMPLE AND CONVENIENT METHOD OF AMINOMETHYLENATION OF 2-ACETYL-SUBSTITUTED CYCLIC BETA-DIKETONES
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[4] CO2 capture capacity of five- and six-membered cyclic amidines bearing silatranyl group under dry conditions
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[5] 2+1 resonance enhanced multiphoton ionization spectroscopy as a tool for stereochemical and conformational analysis of substituted five- and six-membered rings
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Baer, T
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[6] Aminoketyl Radicals in Organic Synthesis: Stereoselective Cyclization of Five- and Six-Membered Cyclic Imides to 2-Azabicycles Using SmI2-H2O
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[7] Pd-Catalyzed Decarbonylative sp2 C-H Arylation: Construction of Five- and Six-Membered (Hetero)Cyclic Compounds
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[8] Five- and six-membered cyclic α-acylvinyl anionic synthons: Synthesis of α-trimethylsilyl-α,β-unsaturated cycloalkenones and their conversion into 2-(hydroxydimethylsilyl)cycloalk-2-enones through carbon-silicon bond scission
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[9] Difference between 2JC2H3 and 2JC3H2 spin-spin couplings in heterocyclic five- and six-membered rings as a probe for studying σ-ring currents: a quantum chemical analysist
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dos Santos, Francisco P.
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[10] An efficient synthesis of optically active five- and six-membered cyclic compounds with selectable stereo-controls by a Ti(II)-mediated cyclization of chiral secondary 2,7-and 2,8-enyn-1-ol derivatives
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Takayama, Y
Okamoto, S
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TETRAHEDRON LETTERS, 2003, 44 (04) : 653 - 657

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