82408-26-2Relevant academic research and scientific papers
Photoinduced Ring-opening Reaction of 1-(2-Naphthoyl)aziridine in Various Halogenated Hydrocarbons
Nishimoto, Sei-ichi,Izukawa, Tsukuru,Kagiya, Tsutomu
, p. 2937 - 2941 (1982)
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.
Selective Photorearrangement of 1-(2-Naphthoyl)aziridine to 2-(2-Naphthyl)-2-oxazoline by Polybromobenzenes
Nishimoto, Sei-ichi,Izukawa, Tsukuru,Kagiya, Tsutomu
, p. 1147 - 1152 (2007/10/02)
Photoreactions of 1-(2-naphthoyl)aziridine (1) in the presence of various brominated hydrocarbons (4a-f) in deaerated benzene solution have been studied at room temperature.The selective photorearrangement of (1) to 2-(2-naphthyl)-2-oxazoline (2) was promoted by 1,3,5-tribromobenzene (4a) and 1,4-dibromobenzene (4b).The nonpolar solvent benzene favoured selective photorearrangement, compared with polar acetonitrile.The series of brominated hydrocarbons (4a-e) but not CH3(CH2)2Br (4f) formed 1:1 ground-state complexes with (1).The fluorescence emission of (1) was quenched efficiently by (4a-f).The fluorescence-quenching rate constant (kq) increased on increasing the half-wave reduction potential (Ered1/2) of (4a-f).The photosensitized triplet reaction of (1) did not give (2) but a small amount of oligomer.The reciprocal of the quantum yield for the photorearrangement (Φ-1) was proportional to that of the concentration of non-complexed (4a) free)-1>.
