Synthesis and Characterization of New Boron Compounds Using Reaction of Diazonium Tetraphenylborate with Enaminoamides
Markéta Svobodová,
Jan Svoboda,
Bing-Han Li,
Valerio Bertolasi,
Luboš Socha,
Miloš Sedlák,
Lukáš Marek
Affiliations
Markéta Svobodová
Faculty of Chemical Technology, Institute of Organic Chemistry and Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic
Jan Svoboda
Faculty of Chemical Technology, Institute of Organic Chemistry and Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic
Bing-Han Li
Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan
Valerio Bertolasi
Department of Chemical and Pharmaceutical Sciences, University of Ferrara, Via L. Borsari 46, 44121 Ferrara, Italy
Luboš Socha
Faculty of Chemical Technology, Institute of Organic Chemistry and Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic
Miloš Sedlák
Faculty of Chemical Technology, Institute of Organic Chemistry and Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic
Lukáš Marek
Faculty of Chemical Technology, Institute of Organic Chemistry and Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic
A family of oxazaborines, diazaborinones, triazaborines, and triazaborinones was prepared by reaction of polarized ethylenes, such as β-enaminoamides, with 4-methylbenzenediazonium tetraphenylborates. The reaction conditions (stirring in CH2Cl2 at room temperature (Method A) or stirring with CH3COONa in CH2Cl2 at room temperature (Method B) or refluxing in the CH2Cl2/toluene mixture (Method C)) controlled the formation and relative content of these compounds in the reaction mixtures from one to three products. Substituted oxazaborines gradually rearranged into diazaborinones at 250 °C. The prepared compounds were characterized by 1H NMR, 13C NMR, IR, and UV–Vis spectroscopy, HRMS, or microanalysis. The structure of individual compounds was confirmed by 11B NMR, 15N NMR, 1D NOESY, and X-ray analysis. The mechanism of reaction of enaminoamides with 4-methylbenzenediazonium tetraphenylborate was proposed.
