Journal of the Chemical Society. Perkin transactions I p. 2173 - 2177 (1996)
Update date:2022-08-05
Topics:
Morgan, Jacqueline
Hambley, Trevor W.
Pinhey, John T.
(6-Methoxy-2,3,4-trimethylphenyl)phenyllead diacetate 17, the methyl ether of one of the two possible intermediates in the ortho phenylation of 3,4,5-trimethylphenol by phenyllead triacetate, is synthesised and shown to be unchanged in CHCl3-pyridine at 60°C even after 6 days, thus excluding diaryllead diacetates as intermediates in this supposed ligand coupling process. A study of the arylation of a number of methyl substituted phenols by p-methoxyphenyllead triacetate shows that, in general, the rate of ortho arylation increases with methyl substitution; however, ortho methyl groups have a much greater effect than those in the meta and para positions. These results support the view that the arylation of phenols proceeds by an initial ligand exchange (or ligand exchange and pseudorotation) to produce an intermediate in which π-donation by the aryloxy ligand and electron release to the ortho position(s) are important factors. Phenols which are poor π-donors do not undergo the reaction.
View MoreAstaTech ( Chengdu) BioPharmaceutical Corp.
website:http://www.astabiochem.cn/
Contact:+86-15198215156-15198215156
Address:SICHUAN CHENGDU
JiangXi Hong Run Chemical Co., Ltd
Contact:+86-0791-88521351
Address:XingHuo industrial zone in YongXiu county
Contact:+86-0512-69209969
Address:Room 317,Lushan Road,Suzhou New District,Jiangsu Province,China.
shanghai jinshan pharmaceutical Co.,Ltd
Contact:021-57363011，13681638167
Address:No. 7966 Tingfeng Road,Jinshan,Shanghai,China
Contact:+44 (0)2036089360-31
Address:Chanceryhouse,Chancery Lan
Doi:10.1021/ja9608555
(1996)Doi:10.1246/cl.1996.965
(1996)Doi:10.1016/j.tetlet.2016.09.060
(2016)Doi:10.1271/bbb.65.1284
(2001)Doi:10.1021/j100239a017
(1983)Doi:10.1139/v68-006
(1968)
