TY - JOUR
T1 - Dehydrochlorination of 1,1,1,3,3-Pentachlopropane promoted by fluoride
AU - Zhang, Chengping
AU - Zhang, Tongyun
AU - Ma, Xiaoxun
AU - Quan, Hengdao
N1 - Publisher Copyright:
© 2022
PY - 2022/9
Y1 - 2022/9
N2 - The dehydrochlorination of 1,1,1,3,3-pentachloropropane (HCC-240fa) with alkali metal halide in amide to produce tetrachloropropene isomers was taken into investigation. Studies found that E-1,3,3,3-tetrachloropropene (HCO-1230zd(E)), Z-1,3,3,3-tetrachloropropene (HCO-1230zd(Z)) and 1,1,3,3-tetrachloropropene (HCO-1230za) were formed by the selective dehydrochlorination promoted by halide anions, where fluoride had the best reactivity among the four kinds of halide anions. Besides, it was also found when the molecular polarity index (MPI) of the amide was greater than or equal to 14.3 kcal/mol, it was conducive to the dehydrochlorination reaction, and the conversion was close to 100%. Additionally, DFT calculations demonstrated that the selective dehydrochlorination at the 1-position and 2-position of HCC-240fa was easier than that at the 2-position and 3-position, which is consistent with the experimental results.
AB - The dehydrochlorination of 1,1,1,3,3-pentachloropropane (HCC-240fa) with alkali metal halide in amide to produce tetrachloropropene isomers was taken into investigation. Studies found that E-1,3,3,3-tetrachloropropene (HCO-1230zd(E)), Z-1,3,3,3-tetrachloropropene (HCO-1230zd(Z)) and 1,1,3,3-tetrachloropropene (HCO-1230za) were formed by the selective dehydrochlorination promoted by halide anions, where fluoride had the best reactivity among the four kinds of halide anions. Besides, it was also found when the molecular polarity index (MPI) of the amide was greater than or equal to 14.3 kcal/mol, it was conducive to the dehydrochlorination reaction, and the conversion was close to 100%. Additionally, DFT calculations demonstrated that the selective dehydrochlorination at the 1-position and 2-position of HCC-240fa was easier than that at the 2-position and 3-position, which is consistent with the experimental results.
KW - 1,1,3,3-tetrachloropropepene
KW - 1,3,3,3-tetrachloropropene
KW - DFT
KW - Dehydrochlorination
KW - N,N-dimethylformamide
UR - http://www.scopus.com/inward/record.url?scp=85135048377&partnerID=8YFLogxK
U2 - 10.1016/j.jfluchem.2022.110020
DO - 10.1016/j.jfluchem.2022.110020
M3 - Article
AN - SCOPUS:85135048377
SN - 0022-1139
VL - 261-262
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
M1 - 110020
ER -