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 MoreWeifang Jahwa Chemical Co.,Ltd
Contact:0086-536-8897731,8897730
Address:No.5166 East Dongfeng Street,Weifang,Shandong,China
website:http://www.acrospharmatech.com
Contact:+1-3234804688
Address:Flat/RM 1502,Easey Commercial building 253-261 Hennessy Road,Wanchai,HongKong
Contact:86-311-67265101
Address:203 Lianmeng Road, Qiaoxi District
Xian Changyue Biological Technology Co., Ltd.
website:https://www.xachangyue.com/
Contact:+86-029-62886900
Address:Keji Road NO.70
hangzhou verychem science and technology co.ltd
website:http://www.verypharm.com
Contact:+86-571-88162785; 88162786
Address:F1502, 753 Shenhua road, Hangzhou, 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)