Formation and Stability of the 4-Methoxyphenonium Ion in Aqueous Solution

被引：6

作者：

Tsuji, Yutaka ^{[2
]}

Hara, Daisuke ^{[2
]}

Hagimoto, Rui ^{[2
]}

Richard, John P. ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

[2] Kurume Natl Coll Technol, Dept Biochem & Appl Chem, Kurume, Fukuoka 8308555, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 23期

基金：

美国国家卫生研究院;

关键词：

SUBSTITUTION; REACTIVITIES; GENERATION; LIFETIMES; CARBON;

D O I：

10.1021/jo202118s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-methoxyphenylethyl tosylate (MeO-1-Ts) is first-order in [N-3(-)]. A carbon-13 NMR analysis of the products of the reactions of MeO-1-[alpha-C-13]Ts shows the formation of MeO-1-[beta-C-13]OH and MeO-1-[beta-C-13]N-3 from the trapping of a symmetrical 4-methoxyphenonium ion reaction intermediate 2(+). An analysis of the rate and product data provides a value of k(az)/k(s) = 83 M-1 for partitioning of 2(+) between addition of azide ion and solvent. These data set a limit for the lifetime of 2(+) in aqueous solution.

引用

页码：9568 / 9571

页数：4

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