Hojo, M., Masuda, R. and Okada, E. (1987) A Convenient and Facile Synthesis of Fluorine-Containing 1H+, 2H-Bennz[g]indazoles and Naphthisoxazoles by Aromatic Nucleophilic N-N-Exchange Reaction of N,N-Dimethyl-2,4-bis(trifluoroacetyl)- 1-naphthylamine with Hydrazines and Hydroxylamine. Synthesis, 1990, 481-483.
https://doi.org/10.1055/s-1990-26911

has been cited by the following article:

• TITLE: Computational Study for the Aromatic Nucleophilic Substitution Reaction on 1-Dimethylamino-2,4-bis(trifluoroacetyl)-naphthalene with Amines

  AUTHORS: Norio Ota, Tomohiro Nakada, Takumi Shintani, Yasuhiro Kamitori, Etsuji Okada

  KEYWORDS: 1-Amino-2, 4-bis(trifluoroacetyl)naphthalenes, Aliphatic Amines, Meisenheimer Complexes, Aromatic Nucleophilic Substitution, DFT Calculation

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.8 No.3, August 2, 2018

  ABSTRACT: Our previous research showed that aliphatic amines were put in order of high reactivity as “ethylamine > ammonia > t-butylamine > diethylamine” on the aromatic nucleophilic substitution of 1-dimetylamino-2,4-bis(trifluoroacetyl)-naphthalene 1 in acetonitrile. The DFT calculation study (B3LYP/6-31G* with solvation model) for the reactions of 1 with above four amines rationally explained the difference of each amines reactivity based on the energies of their Meisenheimer complexes 3 which are assumed to formed as the reaction intermediates in the course of the reaction giving the corresponding N-N exchange products 2. Intramolecular hydrogen bond between amino proton in 1-amino group and carbonyl oxygen in 2-trifluoroacetyl group stabilizes Meisenheimer complexes 3 effectively, and accelerates the substitution reaction from 1 to 2. Our calculation results also predicted that the above order of amines is also true if less polar toluene is used as a solvent instead of acetonitrile even though more enhanced conditions are required.