Journal of the Chemical Society. Perkin transactions II p. 847 - 852 (1986)
Update date:2022-08-03
Topics:
Keumi, Takashi
Morita, Toshio
Shimada, Takanobu
Teshima, Naomi
Kitajima, Hidehiko
Prakash, G. K. Surya
Facile transacylation between acylpentamethylbenzene and activated arenes such as anisole was found to occur in boiling trifluoroacetic acid (TFA).The mechanism for the transacylation between acetylpentamethylbenzene (AcPMB) and anisole with TFA was elucidated by means of product isolation and kinetics.The reaction proceeds via reversible protodeacetylation of AcPMB involving an ipso-protonated intermediate B to give pentamethylbenzene and acetic trifluoroacetic anhydride followed by irreversible acetylation of anisole by the mixed anhydride.The mechanism resulting in an ipso-protonated intermediate B was deduced from the reaction of acetylmesitylene with <2H>TFA as well as from the rate of deacetylation of 3,5-dideuterioacetylmesitylene with TFA.The formation of such an intermediate was also independently confirmed by 13C n.m.r. spectroscopic syudies on AcPMB in superacid solutions under stable conditions.
View MoreKINHENG CHEMICAL(SHANGHAI)CO., LTD.
Contact:+8621-60490170
Address:Room401, No.28,Lane 189, Yangshupu Rd. Shanghai, China.
Shanghai Micro-mega Industry Co., Ltd.
Contact:0086-21-34628682;57153848
Address:Rm413,No.413,West Meilong Road, Minhang District,Shanghai P R China
Zibo Fuxi'er Chemical Co.,Ltd （Shanxian Fuxi'er Chemical Co.,Ltd）
Contact:+86-533-2091422
Address:Eastern 4 on the 3th Road ,Liangxiang Industrial Park, Zibo city ,Shandong,China
Contact:86-931-8272767
Address:Room 602, No.461, Nanchang Road, Chengguan District, Lanzhou City, China PRC
Contact:+86-22-26358246
Address:601-4-20, Fujiayuan, Tiantai Road, Hebei District, Tianjin, China
Doi:10.1016/j.bmc.2015.06.040
(2015)Doi:10.1002/recl.19730921113
(1973)Doi:10.1016/j.dyepig.2016.03.023
(2016)Doi:10.1039/b803626h
(2008)Doi:10.1002/chem.201102279
(2012)Doi:10.1246/bcsj.59.503
(1986)
