27210-64-6Relevant academic research and scientific papers
Photosubstitution of 1-Methoxy-4-nitronaphthalene with Amine Nucleophiles: Dual Pathways
Bunce, Nigel J.,Cater, Stephen R.,Scaiano, J. C.,Johnston, Linda J.
, p. 4214 - 4223 (2007/10/02)
The photosubstitution of 1-methoxy-4-nitronaphthalene (MNN) with amines has been investigated by a combination of continuous and time-resolved experiments.Primary amines cause replacement of the nitro group, while secondary amines displace the methoxy substituent.Both reactions involve attack of the amine upon the triplet excited state of MNN.Spectroscopic evidence for the radical anion MNN*- has been obtained; the yield of this species depends upon the structure of the amine in the order RNH2*-, but that the reaction with primary amines is most probably an example of an SN2 Ar* process.The results for MNN and related compounds are discussed in the context of the orientation rules proposed by Mutai et al.
