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Selective Photorearrangement of 1-(2-Naphthoyl)aziridine to 2-(2-Naphthyl)-2-oxazoline by Polybromobenzenes

DOI: 10.1039/P29830001147

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1147 - 1152 (1983)

Update date:2022-08-05

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Authors:

Nishimoto, Sei-ichiNishimoto, Sei-ichi

Izukawa, TsukuruIzukawa, Tsukuru

Kagiya, TsutomuKagiya, Tsutomu

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Article abstract of DOI:10.1039/P29830001147

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) <(<(4a)>free)-1>.

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Product name:1-(2-naphthoyl)aziridine-bromobenzene 1:1 complex

Cas No:88099-86-9

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