M. Minabe, S. Takeshige, Yuuji Soeda
1994
Citations
1
Influential Citations
15
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Bromination and the Friedel–Crafts acetylation of monosubstituted pyrenes were examined. Acetylation of 1-acetyl- and 1-ethylpyrene occurred at the 8-, 6-, or 3-position, but the reaction of 1-methoxypyrene afforded only the 8- and 6-acetyl derivatives. By acetylation, 4-acetylpyrene yielded the 1- and 6-acetyl compounds, and 4-ethylpyrene gave the 6- and 8- derivatives. Also, 4-bromopyrene afforded the corresponding 8-, 6-, and 1-acetyl derivatives by the same reaction. Bromination of 1-ethyl- and 4-ethylpyrene yielded the 8- and 6-bromides, but the reaction of 1-nitro- and 1-bromopyrene took place at the 6-, 8-, or 3-position. The formation ratio of these regioisomers differs by the substituents. The regioselectivity on the acetylation accords in some degree with the prediction based on the 13C NMR chemical shift of each position. The relative rates of these electrophilic substitutions correlate to the substituent constant, σ+, of the substituent attached to the pyrene.