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peri-Naphthylenediamines

22. Synthesis of 1,4,5-tris(dimethylamino)naphthalene and other “proton sponge” 4-amino derivatives

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Catalytic hydrogenation of 4-nitro-1,8-bis(dimethylamino)naphthalene afforded the previously unknown 1-amino-4,5-bis(dimethylamino)naphthalene, subsequent methylation of which gave 1-methylamino and 1-dimethylamino “proton sponge” derivatives. The pK a values of 1-amino-, 1-methylamino-, and 1-dimethylamino-4,5-bis(dimethylamino)-naphthalenes estimated by1H NMR in DMSO-d6 are equal to 9.8, 10.1, and 8.0, respectively.

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Authors and Affiliations

  1. Rostov State University, 7 ul. zorge, 344090, Rostov-on-Don, Russian Federation

    V. A. Ozeryanskii & A. F. Pozharskii

Authors
  1. V. A. Ozeryanskii
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  2. A. F. Pozharskii
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Additional information

For Part 21, see Ref. 1.

Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 8, pp. 1501–1504, August, 1997.

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Ozeryanskii, V.A., Pozharskii, A.F. peri-Naphthylenediamines. Russ Chem Bull 46, 1437–1440 (1997). https://doi.org/10.1007/BF02505681

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  • DOI: https://doi.org/10.1007/BF02505681

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