Investigation in the series of substituted butan- and butenolides: XV. Transformations of 4-hydroxy-2-butenolide in water media at various pH values

被引：6

作者：

Strizhov, NK ^{[1
]}

Poskonin, VV ^{[1
]}

Badovskaya, LA ^{[1
]}

Kupina, EP ^{[1
]}

机构：

[1] Kuban State Technol Univ, Krasnodar 350072, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 38卷 / 02期

关键词：

D O I：

10.1023/A:1015578003374

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 4-hydroxy-2-butenolide was established by polarographic method to undergo in water solutions fast tautomeric and acid-base transformations. Depending on pH of the medium the compound is present either as a cyclic irreducible form (at pH 0-4) or in the open-chain (carbonyl-containing) reducible forms (at pH > 4 and < 0). It is presumed that in going from the basic to strongly acidic medium and backwards occur consecutive equilibrium transitions of four species: cis-beta-formylacrylic acid anion (A-), its neutral molecule (HA) existing as linear and cyclic tautomers, and protonated forms (H(2)A(+) and H(3)A(+)). The formation mechanism thereof is considered.

引用

页码：251 / 255

页数：5

共 3 条

[1] Investigation in the Series of Substituted Butan- and Butenolides: XV. Transformations of 4-Hydroxy-2-butenolide in Water Media at Various pH Values
N. K. Strizhov
V. V. Poskonin
L. A. Badovskaya
E. P. Kupina
Russian Journal of Organic Chemistry, 2002, 38 : 251 - 255
[2] Study in a series of substituted butanolides and butenolides .12. Synthesis of 4-substituted 2-butenolides and 2-butenic acids based on 4-hydroxy-2-butenolide and its tautomeric forms
Poskonin, VV
Badovskaya, LA
Butin, AV
ZHURNAL ORGANICHESKOI KHIMII, 1997, 33 (04): : 574 - 578
[3] INVESTIGATION IN SUBSTITUTED BUTANOLIDES AND BUTENOLIDES SERIES .5. SYNTHESIS OF 4-HYDROXY-2-BUTEN-4-OLIDE AND ITS DERIVATIVES BASED ON THE REACTION OF FURFURAL WITH HYDROGEN-PEROXIDE
POSKONIN, VV
BADOVSKAYA, LA
GAVRILOVA, SP
KULNEVICH, VG
ZHURNAL ORGANICHESKOI KHIMII, 1989, 25 (08): : 1701 - 1706

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