| Summary: | 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 CH<sub>2</sub>Cl<sub>2</sub> at room temperature (Method A) or stirring with CH<sub>3</sub>COONa in CH<sub>2</sub>Cl<sub>2</sub> at room temperature (Method B) or refluxing in the CH<sub>2</sub>Cl<sub>2</sub>/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 <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR, and UV–Vis spectroscopy, HRMS, or microanalysis. The structure of individual compounds was confirmed by <sup>11</sup>B NMR, <sup>15</sup>N NMR, 1D NOESY, and X-ray analysis. The mechanism of reaction of enaminoamides with 4-methylbenzenediazonium tetraphenylborate was proposed.
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