Abstract
Reaction of 2-phenyl-1,3,2-benzodiazaborolidine ( 2) with benzoyl chloride afforded N,N′-dibenzoyl-o-phenylenediamine ( 8) regardless of the amount of the acid chloride employed. Depending on the work-up procedure, the 2-phenylboron moiety was isolated as either phenylboronic acid or phenylboronic acid anhydride. In the absence of added bases, the reaction was observed to be susceptible to solvent assistance by ethers, presumably by coordination with the empty p-orbital of boron. In the presence of added amines, the extent of benzoylation was altered considerably. With pyridine as a co-reagent, small amounts of 1,3-dibenzoyl-2-phenyl-1,3,2,-benzodiazaborolidine mono- or dihydrocholoride were isolated though this compound readily underwent hydrolysis or oxidation upon standing. Interaction of 2 with sodium hydride in tetrahydrofuran caused ionization of only one of the two hydrogens bound to nitrogen even upon extended reflux. Benzoylation of the heterocycle under these latter conditions again afforded only the dibenzoylated compound 8.
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