SN2 substitution on sp2 nitrogen of protonated oxime

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

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)


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
Publication statusPublished - 1998


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