Regioselectivity of aryl azide cycloaddition to methyl propiolate in aqueous media: experimental evidence versus local DFT HSAB principle

被引：19

作者：

Molteni, Giorgio ^{[1
]}

Ponti, Alessandro

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, Via Golgi 19, I-20133 Milan, Italy

[2] CNR, Ist Sci & Tecnol Mol, I-20133 Milan, Italy

来源：

ARKIVOC | 2006年

关键词：

1,3-dipolar cycloaddition; azides; hard-soft acid-base principle; density functional theory;

D O I：

10.3998/ark.5550190.0007.g06

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselectivity of the 1,3-dipolar cycloaddition of a series of 4-substituted-phenyl azides to methyl propiolate in aqueous medium has been determined experimentally. Ab initio B3LYP/6-311+G(d,p) calculations in conjunction with the local HSAB principle developed within density functional theory provided a full rationalization of cycloaddition regioselectivity.

引用

页码：49 / 56

页数：8