N,N,N′-Trialkyl-1,8-diaminonaphthalenes: convenient method of preparation from protonated proton sponges and the first X-ray information |
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Authors: | V.A. Ozeryanskii A.F. Pozharskii D.A. Shevchuk A.N. Chekhlov O.A. Dyachenko |
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Affiliation: | a Department of Organic Chemistry, Rostov State University, Zorge 7, 344090 Rostov-on-Don, Russian Federation b Institute of Problems of Chemical Physics, Russian Academy of Sciences, Institutski 18, 142432 Chernogolovka, Moscow Region, Russian Federation |
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Abstract: | A simple procedure for the synthesis of N,N,N′-trialkyl-1,8-diaminonaphthalenes is described. It consists in partial demethylation (dealkylation) of commercially available proton sponge [1,8-bis(dimethylamino)naphthalene] and some of its derivatives at heating with HBr-KI-DMF system. Limitation, scope and a possible mechanistic pathway for the reaction are discussed. For isomeric 8-dimethylamino-1-methylamino- and 1-dimethylamino-8-methylamino-4-nitronaphthalenes, X-ray measurements have been conducted. The first examples of complete realkylation reactions in the naphthalene proton sponges are reported. |
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Keywords: | Proton sponges N,N,N&prime -Trialkyl-1,8-diaminonaphthalenes Demethylation Dealkylation Realkylation Intramolecular hydrogen bond Nitronaphthalenes Molecular and crystal structures |
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