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 MoreContact:0091-265-2313036
Address:311, ATLANTIS HEIGHTS SARABHAI MAIN ROAD,VADIWADI ,VADODARA
Shanghai doly chemical Co.,Ltd
Contact:+86-21-34716221
Address:No.328,WuHe Roard,MinHang,ShangHai China
website:http://www.amadischem.com
Contact:86-571-89925085
Address:Watts Cosine.No.166.Xiangmao Road.
Jiangsu Fengshan Group Co., Ltd.
Contact:86-25-86558671
Address:1903,Central International Mansion 105-6 North Zhongshan Road, Nanjing, China
Rudong Zhenfeng Yiyang Chemical Co., Ltd.
Contact:0513-84573047
Address:South Fengli Town, Rudong County, Jiangsu Province, 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)