NMR Study of the Tautomeric Behavior of N-(α-Aminoalkyl)tetrazoles

被引：25

作者：

Katritzky, Alan R. ^{[1
]}

El-Gendy, Bahaa El-Dien M. ^{[1
,2
]}

Draghici, Bogdan ^{[1
]}

Hall, C. Dennis

Steel, Peter J. ^{[3
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Benha Univ, Fac Sci, Dept Chem, Banha, Egypt

[3] Univ Canterbury, Dept Chem, Christchurch 8140, New Zealand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 19期

关键词：

N-SUBSTITUTED BENZOTRIAZOLES; TETRAZOLE DERIVATIVES; CHEMISTRY; MECHANISM;

D O I：

10.1021/jo101195z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(alpha-Aminoalkyl)tetrazoles exist in solution as equilibrium mixtures of N1 and N2 tautomers. The position of equilibrium depends significantly on the polarity of the solvent and the substituents in the tetrazole ring. Interconversion between individual tautomers is shown to proceed via tight ion-pair intermediates in which intramolecular recombination is faster than the intermolecular crossover since the latter probably requires solvent separation of ion-pair intermediates.

引用

页码：6468 / 6476

页数：9

共 38 条

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