ChemInform Abstract: Stereoselective Addition of Acetone to the C=N Bond of [4.3.0] Boron...
1
2002 organo-boron compounds organo-boron compounds S 0040 06 - 188 Stereoselective Addition of Acetone to the C=N Bond of [4.3.0] Boron Heterobicycles. — New boron heterocycles (III), prepared by reaction of equimolar amounts of iminodiphenols (I) with phenylboronic acid in THF, undergo an acetolysis reaction to give the corresponding dioxazaborocines (V), containing all substituents (H–N, Ph, CH 2 COMe) in a cis configuration, in good yields. It is found that the coordination of the nitrogen atom to boron in derivatives (III) is responsible for the polarization of the C=N bond and for the stereoselective reaction with acetone. By change from THF to EtOH as solvent in the reaction of iminophenol (Id) with acid (II), compound (VII) is formed. — (BARBA, VICTOR; CUAHUTLE, DAMIAN; SANTILLAN, ROSA; FARFAN, NORBERTO; Can. J. Chem. 79 (2001) 8, 1229-1237; Dep. Quim., Cent. Invest. Estud. Avanzados, Inst. Politec. Nac., 07000 Mexico, Mex.; EN) 1
-
Upload
victor-barba -
Category
Documents
-
view
214 -
download
2
Transcript of ChemInform Abstract: Stereoselective Addition of Acetone to the C=N Bond of [4.3.0] Boron...
![Page 1: ChemInform Abstract: Stereoselective Addition of Acetone to the C=N Bond of [4.3.0] Boron Heterobicycles.](https://reader042.fdocuments.net/reader042/viewer/2022020508/575003841a28ab1148999ae9/html5/page/1.jpg)
2002 organo-boron compounds
organo-boron compoundsS 0040
06 - 188Stereoselective Addition of Acetone to the C=N Bond of [4.3.0]Boron Heterobicycles. — New boron heterocycles (III), prepared byreaction of equimolar amounts of iminodiphenols (I) with phenylboronic acid inTHF, undergo an acetolysis reaction to give the corresponding dioxazaborocines(V), containing all substituents (H–N, Ph, CH2COMe) in a cis configuration,in good yields. It is found that the coordination of the nitrogen atom to boronin derivatives (III) is responsible for the polarization of the C=N bond andfor the stereoselective reaction with acetone. By change from THF to EtOHas solvent in the reaction of iminophenol (Id) with acid (II), compound (VII)is formed. — (BARBA, VICTOR; CUAHUTLE, DAMIAN; SANTILLAN,ROSA; FARFAN, NORBERTO; Can. J. Chem. 79 (2001) 8, 1229-1237; Dep.Quim., Cent. Invest. Estud. Avanzados, Inst. Politec. Nac., 07000 Mexico,Mex.; EN)
1
