1,3-bis(2,4,6-trinitrophenylaminooxy)propane and its 4-cyano-2,6-dinitrophenyl congener: Synthesis and properties |
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| Authors: | Irina C Covaci Petre Ionita Miron T Caproiu Radu Socoteanu Titus Constantinescu Alexandru T Balaban |
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| Institution: | (1) Roumanian Academy, Institute of Physical Chemistry “I.G. Murgulescu”, Laboratory of Supramolecular Chemistry and Interphase Processes, Splaiul Independentei 202, 77408 Bucharest, Roumania;(2) Roumanian Academy, Institute “C. D. Nenitzescu” of Organic Chemistry, Splaiul Independentei 202B, 77408 Bucharest, Roumania;(3) Department of Organic Chemistry, University “Polytechnica”, Faculty of Industrial Chemistry, Bucharest, Roumania;(4) Texas A&M University at Galveston, 77553-1675 Galveston, TX, USA |
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| Abstract: | Starting from N-hydroxyphthalimide (5) and 1,3-dibromopropane (6) we obtained 1,3-bis(phthalimidooxy)propane (7) which led
to 1,3-bis(aminooxy)propane dihydrochloride (8). From its reaction with picryl chloride or 4-cyano-2,6-dinitrochlorobenzene,
the two title compounds (4b, 4a) were obtained.
1H-NMR and 13C-NMR spectra are presented. For comparison with the analogous N-methoxy-2,6-dinitro-4-R-anilines 1a, 1b (R=CN or R=NO2), wer report the hydrophobic characteristics (by RPTLC), electronic spectra for the neutral compounds and their anions, pK
a
values, and the behavior towards oxidizers (DPPH, PbO2, Pb(CH3COO)4, KMnO4 and Ag2O); DPPH converts compounds 1a, 1b and 4a, 4b into betainic structures 2a, 2b respectively. |
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| Keywords: | N-alkoxyaryl derivatives RPTLC pK a NMR oxidation |
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