THE MECHANISM OF CYCLIZATION OF 1-ETHYL-2-NITROBENZENE TO GIVE 3-METHYLANTHRANIL IN TRIFLUOROMETHANESULFONIC ACID - EVIDENCE FOR AN INTRAMOLECULAR HYDROGEN-TRANSFER

被引：7

作者：

AUSTIN, RP ^{[1
]}

RIDD, JH ^{[1
]}

机构：

[1] UNIV LONDON UNIV COLL,DEPT CHEM,20 GORDON ST,LONDON WC1H 0AJ,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 06期

关键词：

D O I：

10.1039/p29930001229

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deuterium labelling has been used to show that the cyclisation in trifluoromethanesulfonic acid of 1 -ethyl-2-nitrobenzene to 3-methylanthranil does not proceed through an equilibrium concentration of the aci-form of the substrate. Instead, the rate-determining step appears to involve the intramolecular transfer of hydrogen from the alpha-carbon atom to one of the oxygen atoms of the protonated nitro group. This conclusion is supported by semi-empirical molecular orbital calculations.

引用

页码：1229 / 1232

页数：4

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