About the factors which govern the ring-opening of α-lactams with primary amines:: II.: The relative basicity of the amine

被引：2

作者：

Cesare, V ^{[1
]}

Taldone, T ^{[1
]}

Lengyel, I ^{[1
]}

机构：

[1] St Johns Univ, Dept Chem, Jamaica, NY 11439 USA

来源：

HETEROCYCLES | 2002年 / 57卷 / 10期

关键词：

2-alkylaminoamide; aziridinone; regioselective; ring-cleavage;

D O I：

10.3987/COM-02-9585

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring-opening reaction of four stable alpha-lactams, 1-(1-adamantyl)-3,3-di-methylaziridinone (1a), 3-(1-adamantyl)-1-triphenylmethyl-aziridinone (1d), 3-tert-butyl-1-triphenylmethylaziridinone (1e), and 1-(1-adamantyl)-3-tertbutylaziridinone (1g) with some substituted benzylamines and other selected primary amines is described. It emerges from the experimental results that the relative basicity of the amine is a decisive factor in determining regioselectivity in the ring-opening.

引用

页码：1851 / 1868

页数：18

共 16 条

[1]

Albert A., 1984, DETERMINATION IONIZA

[2]

BACKES, 1991, METHODEN ORG CHEM, P1

[3] The preparation and base strengths of some amines [J].