Bulletin of the Chemical Society of Japan p. 172 - 179 (1994)
Update date:2022-08-11
Topics:
Minabe, Masahiro
Takeshige, Shouji
Soeda, Yuuji
Kimura,Takao
Tsubota, Motohiro
Bromination and 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-, of 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, ?+, of the substituent attached to the pyrene.
View MoreHuaihua Baohua Biotechnology Co.,Ltd
website:http://www.baochengchem.com
Contact:86-519-82698291
Address:HouYang chemical development zone,Jintan,Jiangsu,China (213200)
Changzhou Hopschain Chemical Co.,Ltd
Contact:86-519-85528066
Address:Room 710, Unit A, Xingbei Development Mansion, Tongjiang Road, Changzhou City,213000, China
Suzhou Time-chem Technologies Co., Ltd.
Contact:0512-63983931/68086856
Address:No. 1326 of Binhe Road, New District, Suzhou, Jiangsu, P. R. China
XI'AN CHUKANG BIOTECHNOLOGY CO.,LTD
Contact:29-63685658 63685359
Address:Room 3-1202,Building 1,Oriental oasis,East of Xianning Road,Xi'an,Shaanxi 710043 P.R.China
Contact:+86-371-67759225
Address:No.32, Jinsuo Road, High-tech Zone
Doi:10.1039/c6sc00386a
(2016)Doi:10.1002/ejoc.201701749
(2018)Doi:10.1080/00958972.2013.847185
(2013)Doi:10.1248/bpb.b16-00007
(2016)Doi:10.3184/174751918X15411700157951
(2018)Doi:10.1021/ja01138a023
(1952)