TY - JOUR
T1 - Synthesis of hydrohalocyclobutenes through dechlorination of hydrohalocyclobutanes in amide solvents
AU - Zhang, Wenni
AU - Lu, Fengniu
AU - Zhang, Chengping
AU - Guo, Qin
AU - Quan, Hengdao
N1 - Publisher Copyright:
© 2020 Elsevier B.V.
PY - 2020/5
Y1 - 2020/5
N2 - In this study, we synthesized hydrohalocyclobutenes through the dechlorination of hydrohalocyclobutanes in N,N-dimethylformamide and N,N-dimethylacetamide. The structure of the reaction site −CClR1−CClR2– (R1 = H, F; R2 = H, F, Cl) of the reactants was critical for the efficient reductive dechlorination from the 1- and 2- positions. The reaction proceeded efficiently at the –CFCl–CFCl–, –CFCl−CCl2–, and −CHCl−CHCl– groups. Conversely, the –CFCl−CHCl– group could hardly afford the dechlorinated product. Based on these results, we propose a rational reaction mechanism.
AB - In this study, we synthesized hydrohalocyclobutenes through the dechlorination of hydrohalocyclobutanes in N,N-dimethylformamide and N,N-dimethylacetamide. The structure of the reaction site −CClR1−CClR2– (R1 = H, F; R2 = H, F, Cl) of the reactants was critical for the efficient reductive dechlorination from the 1- and 2- positions. The reaction proceeded efficiently at the –CFCl–CFCl–, –CFCl−CCl2–, and −CHCl−CHCl– groups. Conversely, the –CFCl−CHCl– group could hardly afford the dechlorinated product. Based on these results, we propose a rational reaction mechanism.
KW - 1,2-Dichloro
KW - Dechlorination
KW - Elimination
KW - Hydrohalocyclobutenes
KW - N,N-dimethylacetamide
KW - N,N-dimethylformamide
UR - http://www.scopus.com/inward/record.url?scp=85082129273&partnerID=8YFLogxK
U2 - 10.1016/j.jfluchem.2020.109506
DO - 10.1016/j.jfluchem.2020.109506
M3 - Article
AN - SCOPUS:85082129273
SN - 0022-1139
VL - 233
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
M1 - 109506
ER -