Compounds Related to Acridine. VIII. Reaction of 9-Vinylacridine with <i>p</i>-Substituted Nitrosobenzenes

Abstract

Abstract In the presence of hydrochloric acid, 9-vinylacridine reacts with nitrosobenzenes having electron-donating groups such as p-nitroso-N,N-dialkylaminoaniline and p-methylnitrosobenzene to yield a four-membered oxazetidine, as the first example of a non-fluorinated oxazetidine ring system. A new 2:2 adduct, to which the perhydro-1,2,7-oxadiazepine structure is assigned tentatively, is formed in the reaction of 9-vinylacridine with nitrosobenzene or p-chloronitrosobenzene under similar conditions.