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2012 | 10 | 4 | 1119-1136
Tytuł artykułu

New serinolic amino-s-triazines by chemoselective amination of cyanuric chloride and their (pro)diastereomerism in restricted rotational phenomena

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The highly chemoselective preparation of new elaborated N-unsymmetrically substituted chlorodiamino-s-triazines and melamines, seen as building-blocks for iterative synthesis, is reported. It consisted of amination of cyanuric chloride with commercial C-2-substituted 2-aminopropane-1,3-diols (“serinols”), playing the role as “open-chain” unit and enantiopure (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diols (“p-nitrophenylserinols”) based amino-1,3-dioxanes (“closed-chain” unit). Issued from the restricted rotation about C(s-triazine)-N(exocyclic) partial double bonds, seen as axes of (pro)diastereomerism, a global four-component rotational equilibrium involving the title compounds is discussed based on DFT computation and (VT) NMR data. Depending on π-deficiency of the s-triazine core, an (un)synchronised deblocking of the generated rotational diastereomers was observed. They are discussed as influence of intra-vs. intermolecular NH...OH (dynamic) interactions occurring in the “open-chain” unit and the anancomeric, axial vs. equatorial, amino-anchorage of the “closed-chain” unit. [...]
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
10
Numer
4
Strony
1119-1136
Opis fizyczny
Daty
wydano
2012-08-01
online
2012-05-29
Twórcy
  • ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France
autor
  • ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France
autor
  • ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France
  • ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France
  • Department of Organic Chemistry, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania
  • IRCOF — LCOFH, UMR 6014 CNRS COBRA, University and INSA of Rouen, 76821, Mont Saint-Aignan Cedex, France
  • Department of Organic Chemistry, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania, darab@chem.ubbcluj
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-012-0015-4
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