Tetrahedron p. 2349 - 2358 (1996)
Update date:2022-07-29
Topics:
Satoh, Tsuyoshi
Takano, Koji
Ligand exchange reaction of simple aryl α-haloalkyl sulfoxides with alkyllithium and ethylmagnesium halide at low temperature was investigated. On treatment of aryl α-haloalkyl sulfoxide with n-BuLi, t-BuLi, or EtMgX exclusively sulfur-alkyl bond-cleavage took place to afford α-halo carbanion (carbenoid). When this reaction was carried out without a proton source, the intermediate α-halo carbanion decomposed to give olefines in good yield. The ligand exchange reaction of sulfoxide was found to be very fast and the reaction could be carried out with a proton or a deuterium source (internal quench) to afford alkyl halide. This procedure offers a new method for preparing α-deuterated) halides (the halogen is F, Cl, or Br).
View MoreEngineering Research Center of Pesticide, Heilongjiang Province
Contact:+86-451-86609001
Address:No.74 of Xuefu Road, Nangang District,
Frapp's Chemical (NFTZ) Co.,Ltd
Contact:+86-576-86137892
Address:General Chamber of Commercial Building, 159 Wanchang Middle Road, Wenling, Zhejiang, China
NingBO Hong Xiang Biochem.Co.Ltd
website:http://www.hxbiochem.com
Contact:0574-66003444
Address:Ning Bo Bei Lun
Shanghai Massive Chemical Technology Co., Ltd.
website:http://www.massivechem.com/
Contact:+86 21 34943721
Address:Room 435, 4th floor, Building 9, No. 2568 Gudai Road,Minhang District, Shanghai,
Zhonghao (dalian) Research and Design Institute of Chemical Industry Co., Ltd
Contact:+86 411 84674606
Address:201, Huangpu Road , Shahekou District, Dalian ,116023-China
Doi:10.1016/j.tet.2008.07.022
(2008)Doi:10.1016/j.bmcl.2009.04.144
(2009)Doi:10.1021/ic700573j
(2007)Doi:10.1007/BF00954103
(1984)Doi:10.1246/cl.2007.1108
(2007)Doi:10.1007/BF00905695
(1963)