N-烷基-N-酰基邻氯苯胺的光诱导S_(RN)环化

Photoinduced SRN Annulation of N-Alkyl-N-acyl-o-chloroanilino

本文叙述了经邻氯苯胺N-酰基化、还原、N-酰基化和光诱导亲核取代合成N-烷基-3-烷基氧化吲哚的光化学合成路线。N-丙基-N-丁酰基邻氯苯胺在-2.82 V的电化学还原是生成不稳定阴离子游离基的单电子转移过程,奇电子占据C—Cl反键轨道。所以,光诱导的单电子转移和随后的氯离子离去导致双游离基,双游离基分子内偶合成环。

A photochemical synthetic sequence of oxidoindole consisting of N-acylation of o-chloroaniline, reduction, N-acylation and photostimulated nucleopholic annlation has been described. The electrochemical reduction of N-propyl-N-butyryl-o-chloroaniline at-2.82 V has been shown to be an one-electron transfer process forming an unstable radical anion with an Odd electron at σ_(C-Cl)~* bond. Thus, photostimulated single electron transfer in CTC followed by expelling chloride ion leads to a biradical, which couples intramolecularly.