Photoinduced S~R~N annulation of N-alkyl-N-acyl-O-chloroaniline

Acta Chimica Sinica ›› 1992, Vol. 50 ›› Issue (6): 614-619. Previous Articles Next Articles

Original Articles

N-烷基-N-酰基邻氯苯胺的光诱导S~R~N环化

吴国生;陶涛;曹建菁;魏夏凉

中国科学院上海有机化学研究所

发布日期:1992-06-15

Photoinduced S~R~N annulation of N-alkyl-N-acyl-O-chloroaniline

WU GUOSHENG;TAO TAO;CAO JIANJING;WEI XIALIANG

Published:1992-06-15

Abstract

A photochem. synthetic sequence for the preparation of oxoindoles, e.g., I, consisting of N-acylation of o-chloroaniline., reduction, N-acylation and photostimulated nucleophilic annulation is described. The electrochem. reduction of N-propyl-N-butyryl-o-chloroaniline at -2.82 V is a one-electron transfer process forming an unstable radical anion with an odd electron at the s*C-Cl bond.

Key words: INDOLE P, PHOTOCHEMICAL REACTION, REACTION MECHANISM, CYCLIZATION, PHOTOINDUCED

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WU GUOSHENG;TAO TAO;CAO JIANJING;WEI XIALIANG. Photoinduced S~R~N annulation of N-alkyl-N-acyl-O-chloroaniline[J]. Acta Chimica Sinica, 1992, 50(6): 614-619.

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N-烷基-N-酰基邻氯苯胺的光诱导S~R~N环化

Photoinduced S~R~N annulation of N-alkyl-N-acyl-O-chloroaniline

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