h IUCEXT reoort from this Laboratory1 has described an investigation of the reaction of a-diazoacetophenone with sodium methoxide in dilute solution.
We now report on the reactions of a-diazoacetophenone with sodium methoxide in concentrated sclution and with potassium t-butoxide, which have additional features of interest. Addition of an equimolar amount of 7 M methanolic sodium methoxide to 5 M methanolic a-diazoacetophenone led to a violent exothermic reaction which was moderated by external cooling; after tlzree hours the mixture was poured into aqueous sodium bicarbonate. The following products were isolated: 2 methyl benzoate, benaoic acid, (hydrogen cyanide), aceto+enone, %benzoyl-.4phenylpyrazole (I), 3-benzoyl-4-hydroxy-5-phenylpyrazole (II), 3-benzoyl-5hydroxy-4-phenylpy?azole (III), 5-benzoyltetrazole (IV), and a compound C17HllN50' Compounds I -IV were identified by direct compsrison with authentic samples: the preparation of I 1,3 has been described elsewhere; 1 P. Yates and B. L. Shapiro, J. Amer. Chem. Sot. i9, 212 (1959). 2 Satisfactory elementary analyses have been compounds. 3 L. I. Smith and bb. B. Pings, J. Org. Chem.