New Findings in Photochemistry of p-Nitrophenyl Azide in the Presence of an Amine:Generation and Trapping of Enamines
4,5-Dihydro-5-diethylamino-1-(<I>p</I>-nitrophenyl)-1,2,3-triazole (<B>3</B>) was obtained in the photolysis of <I>p</I>-nitrophenyl azide (<B>1</B>) in triethylamine (TEA), for which the structure was determined by X-ray crystallographic analysis. The formation of the triazoline <B>3</B> is reasonably explained in terms of trapping of <I>N,N</I>-diethylvinylamine (<B>5</B>) generated <I>in situ</I> with the starting azide <B>1</B>. The reaction sequence involving a single electron transfer from TEA to the electronically excited azide is proposed for the formation of the enamine <B>5</B>.
- Chemistry letters
Chemistry letters 1999(7), 597-598, 1999-07-05
The Chemical Society of Japan