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Synthesis and Characterization of New Boron Compounds Using Reaction of Diazonium Tetraphenylborate with Enaminoamides.

ABSTRACT: 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.

SUBMITTER: Svobodova M

PROVIDER: S-EPMC8782005 | biostudies-literature |

REPOSITORIES: biostudies-literature

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