Stereoselective addition of acetone to the C=N bond of [4.3.0] boron heterobicycles

Barba, Victor; Cuahutle, Damian; Santillan, Rosa; Farf�n, Norberto
August 2001
Canadian Journal of Chemistry;Aug2001, Vol. 79 Issue 8, p1229
Academic Journal
The reaction of N-salicylidene-2-aminophenolate (SAP-H[sub 2] ) derivatives with phenyl boronic acid afforded five new boron bicyclic species in moderate yields, as confirmed by an X-ray study of the boron heterocycle derived from 2-amino-4-chlorophenol. The results also showed that the boron complexes derived from Schiff bases undergo an acetolysis reaction to give the corresponding dioxazaborocines containing all substituents on the same side also in good yields. The structure of one of the addition products was established by X-ray analysis showing that, in the solid state, it exists as a dimeric structure formed by hydrogen bonds.Key words: borocines, tridentate ligands, imines, boronic acids.La r�action de d�riv�s du N-salicylid�ne-2-aminoph�nolates (SAP-H[sub 2] ) avec l'acide ph�nylboronique conduit, avec des rendements mod�r�s, � la formation de cinq nouvelles esp�ces bicycliques du bore dont la structure a �t� confirm�e par diffraction des rayons X sur l'h�t�rocycle contenant du bore d�riv� du 2-amino-4-chloroph�nol. Les r�sultats montrent aussi que les complexes du bore d�riv�s des bases de Schiff subissent une r�action d'ac�tolyse conduisant � la formation, avec de bons rendements, des dioxazaborocines correspondantes comportant tous les substituants sur le m�me c�t�. La structure de l'un des produits d'addition a �t� d�termin�e par une �tude par diffraction des rayons qui a montr� que, � l'�tat solide, il existe sous la forme d'une structure dim�re form�es par des liaisons hydrog�nes.Mots cl�s : borocines, ligands tridentates, imines, acides boroniques.[Traduit par la R�daction]


Related Articles

  • Dihydrofuropyridines in reactions of pyridoxal imine with 2-chloro-1,3,2-dioxaphosphorinanes. Kibardina, L.; Trifonov, A.; Pudovik, E.; Burilov, A.; Pudovik, M. // Russian Journal of General Chemistry;Feb2015, Vol. 85 Issue 2, p505 

    A letter to the editor in response to the article "Dihydrofuropyridines in reactions of pyridoxal imine with 2-chloro-1,3,2-dioxaphosphorinanes," that was published in a previous issue of the journal is presented.

  • Computational evaluation of the η6-arene during the ATH of imines on Noyori's RuII catalyst. Kacer, Petr; Petr, Sot; Pechacek, Jan; Januscak, Jakub; Kuzma, Marek // Journal of Cheminformatics;2014, Vol. 6 Issue Suppl 1, p1 

    An abstract of the article "Computational evaluation of the Å‹6-arene during the ATH of imines on Noyori's RuII catalyst" by Petr Kacer, Sot Petr, Jan Pechacek, Jakub Januscak and Marek Kuzma is presented.

  • Parallel Screening of Asymmetric Bidentate Ligands in Zinc Catalyzed Transfer Hydrogenation. Zaman, Tariq; Nasir, Habib; Bergin, Enda // Journal of the Chemical Society of Pakistan;2/28/2014, Vol. 36 Issue 1, p85 

    Development in the field of asymmetric catalysis is driven by the importance of stereochemically pure compounds in the field of pharmaceutical industry, agrochemicals and flavors. The unpredictable results given by new catalysts make the design of effective ones a long and costly work....

  • Novel acyclic ligands. Part 1. Synthesis of some... Elsworth, John F.; Msimang, Lorenzo N. // South African Journal of Chemistry;Jun96, Vol. 49 Issue 1/2, p31 

    Part I. Describes the synthesis of compounds incorporating a bis(aminodicarboxamide) residue, which are potential ligands for selected metal ions for use as contrast agents. Information on magnetic resonance imaging; Method to control tissue distribution of the contrast agent; Reaction between...

  • L-selectin-mediated lymphocyte rolling on MAdCAM-1. Berg, E.L.; McEvoy, L.M.; Berlin, C.; Bargatze, R. F.; Butcher, E. C. // Nature;12/16/1993, Vol. 366 Issue 6456, p695 

    Reports on the mucosal vascular addressin MAdCAM-1, a mucosal endothelial adhesion molecule with immunoglobulin- and mucin-like venule (HEV) ligands for the lymphocyte L-selectin homing receptor; Interacting lymphoid cells' display of a `rolling' behavior similar to selectin-dependent rolling of...

  • Tetranuclear hydroxo-bridged copper(II) cluster of the Z type: Preparation and structural and magnetic characterization of [(Cubipy(OH)(BH)(DMSO)]. Dziova, A.; Avdeeva, V.; Polyakova, I.; Malinina, E.; Rotov, A.; Efimov, N.; Minin, V.; Kuznetsov, N. // Doklady Chemistry;Jan2012, Vol. 442 Issue 1, p1 

    The article presents a paper a general procedure for synthesizing hydroxo-bridged copper (Cu II) complexes with the cluster boron anions in the presence of azaheterocyclic ligands. It discusses the structure and magnetic properties of the polymeric chains composed of alternating the first model...

  • Donor-acceptor complexes of linear oligopyrroles with boron trifluoride. Spectral studies and quantum-chemical simulation. Rumyantsev, E. V.; Desoki, A.; Marfin, Yu. S.; Antina, E. V. // Russian Journal of General Chemistry;Sep2010, Vol. 80 Issue 9, p1871 

    Intermediate products of synthesis of the boron trifluoride complexes with linear oligopyrroles are found. By means of electronic spectroscopy it was shown that the reaction of linear oligopyrroles with boron trifluoride in solutions resulted in the formation of stable donor-acceptor complexes....

  • Single-dot spectroscopy of boron and phosphorus codoped silicon quantum dots. Takashi Kanno; Hiroshi Sugimoto; Fucikova, Anna; Valenta, Jan; Minoru Fujii // Journal of Applied Physics;2016, Vol. 120 Issue 16, p164307-1 

    Boron (B) and phosphorous (P) codoped silicon quantum dots (Si QDs) are dispersible in polar solvents without organic ligands, and exhibit size controllable photoluminescence (PL) from 0.85 to 1.85 eV due to the electronic transitions between the donor and the acceptor states. We study the PL...

  • Well-Defined Diimine Copper(I) Complexes as Catalysts in Click Azide-Alkyne Cycloaddition Reactions. Barta, Jordi Markalain; Díez-González, Silvia // Molecules;Aug2013, Vol. 18 Issue 8, p8919 

    A series of 1,4-disubstituted 1,2,3-triazoles have been prepared in high yields while respecting the stringent Click criteria. In these reactions, highly stable pre-formed complexes bearing diimine ligands were used.


Read the Article


Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics