Benzoyl cyanide (I), on treatment with sodium azide in glacial acetic acid, is converted to phenyl isocyanate (Ila). These same reactants in re-butyl alcohol give re-butyl benzoate as the major product. On the other hand, the interaction of benzoyl cyanide and aluminum azide in anhydrous tetrahydrofuran affords 1 -phenyl-5(4H)tetrazolinone (Ilia) (l-phenyl-5-hydroxytetrazole) in 30% yield. The transitory formation of Ila is postulated to explain the latter observation. In accord with this assumption it was found that Ila under the same conditions gave Ilia in 75% yield. In addition, a group of six 1-^-substituted phenyl-5(4H)tetrazolinones (III) have been prepared from the corresponding aryl isocyanate in yields ranging from 58-76%. An acyl halide may be employed instead of an isocyanate as demonstrated by the conversion of acetyl and benzoyl chloride to l-methyl-5(4H)tetrazolinone and Ilia, respectively. Infrared measurements (Nujol) indicate a strong absorption in the carbonyl region (5.83-5.86 µ) of the spectra for each of these tetrazoles. The apparent dissociation constants of III have been measured and compared with values reported for the corresponding 5-arylaminotetrazoles. Ultraviolet absorption studies show characteristic maxima for III in the region of 240-310 m/u.
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