TITLE

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

AUTHOR(S)
Barba, Victor; Cuahutle, Damian; Santillan, Rosa; Farf�n, Norberto
PUB. DATE
August 2001
SOURCE
Canadian Journal of Chemistry;Aug2001, Vol. 79 Issue 8, p1229
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
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]
ACCESSION #
10562285

 

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