Journal of the American Chemical Society p. 7257 - 7267 (1982)
Update date:2022-08-04
Topics:
Tlumak, Robert L.
Day, James C.
Slanga, Joseph P.
Skell, Philip S.
The free-radical isomerization of N-bromosuccinimide to β-bromopropionyl isocyanate has been examined.Of the two varieties of succinimidyl radical (S? or S?), only the ? excited state undergoes the ring opening to the β propionyl isocyanatyl radical.The conversion optimally takes place in >95percent yield.The dependence of NBS concentration along with results obtained from deuterium labeling studies indicate that the ring opening of S? is a reversible process.This explains the failure of N-chlorosuccinimide to produce β-chloropropionyl isocyanate, as well as the increase in ring-opened product for N-bromosuccinimides upon methyl substitution at the 2- and/or 3-position of the succinimidyl ring, since the open-chain radical intermediates are more stable.In the N-bromoglutarimide system, methyl groups on the 2-position are required for the glutarimidyl radicals to undergo the isomerization, ultimately producing isocyanates.The radical-chain nature of these systems is confirmed.
View MoreJiangsu Jiuri Chemical Co.,Ltd.
Contact:+86-519-82118868
Address:Tianwang Town, Jurong City, Jiangsu Province, China
Changsha Huajing Powdery Material Technological Co., Ltd.
Contact:86-731-88879686
Address:Building 2, West Garden, Main Campus of Central South University, Changsha, Hunan Province, China
Wuxi Morality Chemical Co., Ltd
Contact:
Address:B/7F, 321th WuYun Rd, Wanda Plaza, Wuxi City, 214174, China
Contact:0086-27-83607103/83642615
Address:No.498, Jianshe Ave, Wuhan, China
Yantai Derun Liquid Crystal Materials Co. Ltd.
website:http://www.ytderun.com
Contact:86-535-6300169
Address:ROOM 90, XIANGFU STREET, FUSHAN NEW-HIGH-TECH IDUSTRY ZONE, YANTAI
Doi:10.24820/ark.5550190.p010.321
(2018)Doi:10.1039/c39820000416
(1982)Doi:10.1248/cpb.30.1697
(1982)Doi:10.1002/jlac.198519850412
(1985)Doi:10.1016/S0040-4039(00)87315-3
(1982)Doi:10.1021/jo00070a027
(1993)