Journal of Organic Chemistry p. 4764 - 4766 (1995)
Update date:2022-08-23
Topics:
McManus, Samuel P.
Karaman, Rashid M.
Sedaghat-Herati, Reza
Harris, J. Milton
2-(Phenylthio)ethyl chloride specifically deuterated α to the sulfur atom (i.e. 2-Cl) was employed to study the mechanism of displacement of chloride ion by iodide ion in dry acetone solution.Experimental evidence including rate studies has been accumulated that allows the conclusion to be drawn that iodide ion displaces chloride ion from 2-Cl by a classical SN2 mechanism to give 2-I.Under the reaction conditions, however, 2-I is reactive toward anchimerically-assisted ionization which leads to product with the deuterium label scrambled.Reaction of 2-Cl with bromide ion follows a similar course.Our displacement reactions of halide ions by halide ions showed the expected nucleophilicity order of Cl(1-) > Br(1-) > I(1-) and the normal leaving group order of I(1-) > Br(1-) > Cl(1-).An interesting counterion effect was noted with iodides displacing chloride ion.While potassium iodide in acetone converted 2-Cl to the mixture of iodides 2-I and 3-I, tetrabutylammonium iodide caused conversion but the products reverted completely back to the label-scrambled chlorides.The difference in these results is probably because of differences in the thermodynamics of the two systems.
View MoreShandong Yaroma Perfumery Co., Ltd.
Contact:+86- 531- 88024598
Address:7-702 Caizhi Central, 59 Gong Ye South Road, Jinan City,250101, P. R. China
Contact:86+21-56421993
Address:3F,BUILDING 10,NO.2889 JINKE ROAD, SHANGHAI.
Chongqing maohuan Chemicals Co., Ltd
website:http://www.bschem.com
Contact:+86 13996103726
Address:Chongqing Nan'an District Tu Town
Hubei Xinghuo Chemical Co., Ltd.,
Contact:13925817279 13907299441
Address:Xinghuo Fine Chemistry Industrial Park, Xiaochang County, Hubei Province, China
Linyi Shengxin Pharmaceutical R&D Co., Ltd
Contact:+86-18653953873
Address:West First of Yufeng Road, Yishui County
Doi:10.1021/jo00184a002
(1984)Doi:10.1021/jm00141a013
(1981)Doi:10.1246/bcsj.37.1707
(1964)Doi:10.1002/hlca.19760590646
(1976)Doi:10.1039/jr9470000173
(1947)Doi:10.1002/chem.201301590
(2013)