Bulletin of the Chemical Society of Japan p. 757 - 765 (1994)
Update date:2022-07-30
Topics:
Matsuura, Kazunori
Kimura, Yasuo
Takahashi, Hisakazu
Morita, Toshio
Takahashi, Ichiro
et al.
Friedel-Crafts acylation, bromination, deuteration, and nitration of acetylpentamethylbenzene (APMB), 1-acetyl-2,3,4,6-tetramethylbenzene (ATMB), and 1-benzoyl-2,3,4,6-tetramethylbenzene (BTMB) and the resulting product distribution were investigated.Friedel-Crafts acylation, bromination, and deuteration of APMB and Friedel-Crafts acylation of ATMB gave deacetylation-substitution products.On the other hand, bromination and deuteration of ATMB (or BTMB) and Friedel-Crafts acylation of BTMB gave 5-substituted products.In both cases, the positional reactivities were in accordance with the relative ?-complex stability.Conversely, except for Friedel-Crafts-type nitration, the positional reactivities in the nitration of these substrates were strikingly different from those of the above three reactions.Thus, side-chain functionalization at the 6-methyl group occurred in nitration with fuming nitric acid, depending on the solvents in use.The NMDO calculations and the reaction of APMB with single-electron transfer reagents such as tetranitromethane-hν or cerium(IV) ammonium nitrate suggest that the product distribution in nitration can be explained in terms of a single-electron transfer mechanism.
View MoreHuaihua Baohua Biotechnology Co.,Ltd
website:http://www.baochengchem.com
Contact:86-519-82698291
Address:HouYang chemical development zone,Jintan,Jiangsu,China (213200)
Contact:+86-18911665361
Address:Gaoxin district JiNan, China
Shanghai Korey Pharm Co.,Ltd.(expird)
Contact:021-61840961 021-61840962
Address:No.157,Zhuguang Rd, Qingpu, Shanghai, China
Chemsky(shanghai)International Co.,Ltd.
Contact:0
Address:0
website:http://www.apeptides.com/en/
Contact:+86-21-60871011
Address:No. 80 Chuanshan Shuyuan Steet,Pudong,Shanghai
Doi:10.1016/S0040-4020(96)01105-2
(1997)Doi:10.1016/S0960-894X(97)00017-6
(1997)Doi:10.1002/chem.201601623
(2016)Doi:10.1021/ja01097a509
(1953)Doi:10.1080/07328309708006508
(1997)Doi:10.1021/ja01158a090
(1950)