THE AMMONOLYSIS OF BENZIL BY LIQUID AMMONIA¹

The Pyrazines.

“…According to Pinner an intermediate diimine was first produced, which then condensed with some of the diketone present in one of two ways: For completeness, we mention another reaction that may possibly fall in this category: that between benzil and potassium amide in the presence of ammonium chloride, from which traces of tetraphenylpyrazine have been isolated (136).…”

The Chemistry of the Oxazoles.

“…Both of these can be converted to 2,4,5-triphenyloxazole. Ethyl benzoate (55, 126), ammonium benzoate (102), benzamide (49,71,125), a tetraphenylpyrazine derivative (71), diphenylacetylene, diureine when urea is present (11), diphenylimidazole when formaldehyde is present (91), and lophine or 2,4,5-triphenylimidazole (71) have also been isolated.…”

“…Ammonia has been used (a) without other media at room temperature, 35°C., 103°C., and 200°C. (71,111), (b) dissolved in absolute alcohol (20, 70), (c) in 30 per cent aqueous solution with alcohol at room temperature and at 130°C. ( 49), (d) in aqueous solution with alcohol and formaldehyde (91), and (e) in concentrated aqueous solution at 120°C.…”

“…was proposed as the structure for imabenzil. mechanism has been questioned recently by Leslie and Watt(71), who point out that in liquid ammonia the Radziszewski imidazole synthesis gives only a 46 per cent yield of lophine and that as a result it is not necessary to postulate the absence of benzaldehyde during the formation of triphenyloxazole,T h i s c o n t e n t i s o n l y l i c e n s e d f o r c o n s u m p t i o n b y A u t h o r i z e d U s e r s a f f i l i a t e i n d i v i d u a l n o t d i r e c t l y a s s o c i a t e d w i t h s c i t e i s p r o h i b i t e d .…”

Liquid Ammonia Research-1942.

“…An extended study of the interaction of benzil and liquid ammonia or liquid ammonia solutions of potassium amide or ammonium chloride has provided information with regard to the identity and yields of the various products, together with methods for the separation and estimation of these products (37).…”