39139-76-9Relevant academic research and scientific papers
A simple and effective procedure for the N-permethylation of amino-substituted naphthalenes
Sorokin, Vladimir I.,Ozeryanskii, Valery A.,Pozharskii, Alexander F.
, p. 496 - 498 (2007/10/03)
A wide range of amino-substituted naphthalenes can be N-permethylated by the system Me2SO4/Na2CO3/ H2O(alcohols) with good to excellent yields. Steric hindrance does not prevent the reaction. Some amines with electron-withdrawing groups, especially at nonconjugated positions, are also alkylated. The procedure allows the combination of a reduction (catalytic or by tin dichloride in acidic media) and a methylation in a one-pot process. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
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.
peri-NAPHTHYLENEDIAMINES. VI. NITRATION OF 1,8-BIS(DIALKYLAMINO)NAPHTHALENES
Kurasov, L. A.,Pozharskii, A. F.,Kuz'menko, V. V.,Klyuev, N. A.,Chernyshev, A. I.,et al.
, p. 520 - 525 (2007/10/02)
1,8-Bis(dialkylamino)naphthalenes are nitrated by an equimolar amount of nitric acid in sulfuric acid to the para-mononitro derivatives.Nitration of 1,8-bis(dimethylamino)naphthalene cannot be stopped at the formation of the di- and trinitro derivatives, but in the case of 1,8-bis(diethylamino)naphthalene a nitrating mixture makes it possible to realize dinitration.In acetic acid 1,8-bis(dimethylamino)naphthalene is nitrated at once to the 2,4,5,7-tetranitro derivative, while 1,8-bis(diethylamino)naphthalene is converted into a mixture of trinitration and tetranitration products.The unique course of nitration in 1,8-bis(dialkylamino)naphthalenes is due to the basicity of the initial and intermediately formed compounds and also to the reaction medium.
