SN2 substitution on sp2 nitrogen of protonated oxime

Seiji Mori, Katsuya Uchiyama, Yujiro Hayashi, Koichi Narasaka, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

Theoretical studies on intramolecular nucleophilic displacement of the prolonated oxime oxygen willi an aryl ring revealed that the substitution reaction on the sp2 nitrogen atom is a low energy process. This seemingly anomalous substitution is due to the low-lying σ*-orbital of the O-protonated oxime. The theoretical conclusion received experimental support.

Original languageEnglish
Pages (from-to)111-112
Number of pages2
JournalChemistry Letters
Issue number2
DOIs
Publication statusPublished - 1998
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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