613-21-8Relevant articles and documents
SN2 substitution on sp2 nitrogen of protonated oxime
Mori, Seiji,Uchiyama, Katsuya,Hayashi, Yujiro,Narasaka, Koichi,Nakamura, Eiichi
, p. 111 - 112 (2007/10/03)
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.
Synthesis of 8-hydroxyquinolines by the cyclization of m-hydroxyphenethyl ketone O-2,4-dinitrophenyloximes
Uchiyama, Katsuya,Hayashi, Yujiro,Narasaka, Koichi
, p. 445 - 446 (2007/10/03)
8-Hydroxyquinolines are synthesized from O-2,4-dinitrophenyloximes of m-hydroxyphenethyl ketones by the treatment with sodium hydride, and then with 2,3-dichloro4,5-dicyano-p-benzoquinone (DDQ).