Photosubstitution of 1-methoxy-4-nitronaphthalene with amine nucleophiles: dual pathways

…, SR Cater, JC Scaiano, LJ Johnston

Index: Bunce, Nigel J.; Cater, Stephen R.; Scaiano, J. C.; Johnston, Linda J. Journal of Organic Chemistry, 1987 , vol. 52, # 19 p. 4214 - 4223

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Citation Number: 46

Abstract

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 ...