Synthesis of Di and Tetraoximes from the Reaction of Phenylendiamines with Dichloroglyoxime

۲,۵,۱۰,۱۳-Tetraazatricyclo [۱۲,۲,۲,۲۶,۹] icosa-۱(۱۶),۶,۸,۱۴,۱۷,۱۹-hexene-۳,۴,۱۱,۱۲-tetraone tetraoxime (۱a) and ۲,۵,۱۱,۱۴-tetraazatricyclo [۱۳,۳,۱,۱۶,۱۰] icosa-۱(۱۹),۶,۸,۱۰(۲۰),۱۵,۱۷-hexaene-۳,۴,۱۲,۱۳-tetraonetetraoxime (۱b) were obtained from condensation of ۱,۴- and ۱,۳-phenylendiamine with dichloroglyoxime, respectively. The reaction of ۱,۲-phenylendiamine with dichloroglyoxime resulted in the production of (۲Z,۳Z)-۱,۴-dihydroquinoxaline-۲,۳-dione dioxime (۲). The x-ray structure determination of compound ۲ shows the piprazine ring is rather planar relative to the fused aromatic ring. The results show that a resonance occurs between the aromatic ring and the C=N bond, through N۴ and N۳ atoms of the molecule. The results from x-ray data, indicated that the molecules ۲ could exist as a dimmer by intermolecular hydrogen bonding between NH and OH groups.

کلیدواژه ها:

Phenylendiamine ، Dichloroglyoxime ، vic-Dioximes ، Crystal structure ، Intermolecular hydrogen bonds