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 MoreChongqing Changfeng Chemical Co., Ltd.
website:http://www.changfengchem.com
Contact:+86-23-67896333
Address:30th Floor, Longhu Ziduxingzuo Building A, 1st Branch,YuSong Rd., Yubei District, Chongqing, China
Hangzhou Think Chemical Co. Ltd
website:http://www.thinkchem.com/
Contact:86-571-89986307/81956191/81956084/81956192
Address:Room 501-502, Tower E, Yuanjian Building, Yuanyang International Center, Hangzhou-310011, China
Shenzhen Feiming Science and Technology Co,. Ltd
Contact:+86-755-85232577
Address:#B2309, Fenglin International Center ,Jixiang Road, Longcheng street, LongGang District, Shenzhen city, Guangdong province, China.
Hebei Fulong Import & Export Co., Ltd.
Contact:86-311-87795661
Address:15A19 Zhongyuan Building,368 Youyi North Street,Shijiazhuang 050070,China
Changzhou Chenqiang Chemical Co., Ltd
website:http://www.cq-chem.com
Contact:+86-519-88902455
Address:Shanghuang Town, Liyang City
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)