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

Citation
V. Barba et al., Stereoselective addition of acetone to the C=N bond of [4.3.0] boron heterobicycles, CAN J CHEM, 79(8), 2001, pp. 1229-1237
Citations number
34
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
ISSN journal
0008-4042 → ACNP
Volume
79
Issue
8
Year of publication
2001
Pages
1229 - 1237
Database
ISI
SICI code
0008-4042(200108)79:8<1229:SAOATT>2.0.ZU;2-G
Abstract
The reaction of N-salicylidene-2-aminophenolate (SAP-H-2) derivatives with phenyl boronic acid afforded five new boron bicyclic species in moderate yi elds, 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 de rived from Schiff bases undergo an acetolysis reaction to give the correspo nding 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.