Photoinduced Ring-opening Reaction of 1-(2-Naphthoyl)aziridine in Various Halogenated Hydrocarbons

Article abstract of DOI:10.1246/bcsj.55.2937

The in-source photoreaction and the postreaction of 1-(2-naphthoyl)aziridine (NAz) in various halogenated hydrocarbons have been investigated at room temperature under deaerated conditions.Secondary amide such as N-(2-chloroethyl)-2-naphthamide (CENA) or N-(2-bromoethyl)-2-naphthamide (BENA) was obtained along with a rearranged product of 2-(2-naphthyl)-2-oxazoline (NOz).The initial rate of secondary amide formation increased with decreasing dissociation energy of the carbon-halogen bond of halogenated hydrocarbon.The yield of CENA in the postreaction was substantially equal to that of chloride ion formed via the photolyses of chlorinated hydrocarbons.The rearranged product of NOz was confirmed to undergo subsequently photochemical ring-opening reaction to afford CENA or BENA.