Journal of the American Chemical Society p. 3221 - 3225 (1988)
Update date:2022-08-11
Topics:
Tanko, James M.
Skell, Philip S.
Seshadri, Sri
Imidyl radicals react with cyclopropanes solely via hydrogen abstraction.In the case of methylcyclopropane, the major product (cyclopropylcarbinyl bromide) is derived from abstraction of hydrogen from the methyl group.The resultant cyclopropylcarbinyl radical is partioned between two pathways: (1) abstraction of Br from N-bromoimide and (2) rearrangement to the allylcarbinyl radical (eventually yielding 4-bromo-1-butene).Since the absolute rate of the rearrangement is known, an absolute rate constant for the abstraction of Br from N-bromoimides by alkyl radicals can be derived (CH2Cl2 solvent, 15 deg C), k ca. (1.3-1.6)1xE10 M-1s-1.Reactions carried out in the presence of Br2 provide a third pathway for scavenging of the cyclopropylcarbinyl radical, providing kBr2=2.2x1E10 M-1s-1.Thus, trapping of primary R. by either N-bromoimides or Br2 occurs at rates that are diffusion-controlled.
View MoreContact:86-21-57725962
Address:shanghai
Jiangsu Dacheng Pharmaceutical and Chemical Co.,Ltd
Contact:+86-0517-87036900
Address:Chuzhou Chemical park, Huai'an, Jiangsu Province
Arshine Pharmaceutical Co., Limited
website:http://www.cnarshine.com
Contact:0731-88503671
Address:Room 1109.Block C3, Lugu Enterprise Plaza,No.27 Wenxuan Road,Changsha National Hi-Tech Industrial Development Zone,Hunan ,P.R.China
Shanghai Bosman Industrial Co., Ltd
Contact:86-21-63065878-8006
Address:Rm907, No.1611, North Sichuan Road, Hongkou District, Shanghai, 200080 China
shanghai hekang chemical co.ltd
Contact:021-54173790
Address:328 WuHe Road, Building #A, 2nd Floor, Minhang, Shanghai 201109, China
Doi:10.1021/jo00087a044
(1994)Doi:10.1016/j.dyepig.2017.05.021
(2017)Doi:10.1246/cl.2006.252
(2006)Doi:10.1016/0040-4020(95)00071-F
(1995)Doi:10.1016/S0277-5387(00)80121-7
(1993)Doi:10.1016/j.tet.2019.06.004
(2019)