TY - JOUR
T1 - Investigation on Cl-F exchange mechanism occurring at C(sp2) and C(sp3) orbitals of halogenated cyclopentene
AU - Zhang, Chengping
AU - Qing, Feiyao
AU - Quan, Hengdao
AU - Sekiya, Akira
N1 - Publisher Copyright:
© 2016
PY - 2016
Y1 - 2016
N2 - The mechanism of Cl-F exchange of halogenated cyclopentene with AlCl3in dimethylformamide (DMF) or with AlCl4−in 1,1,1,3,3-pentachloropropane (HCC-240fa) was investigated. It was found that in DMF, AlCl3preferred to attack the position with larger electron cloud density relatively like C(sp2) position, which was attributed to that AlCl3was a strong Lewis acid, and in HCC-240fa, AlCl4−preferred to attack the position with smaller electron cloud density relatively like C(sp3) position, which was attributed to that AlCl4−was a Lewis base. Our experimental results showed that Cl-F exchange with AlCl3occurred mainly on C(sp2) atom, and Cl-F exchange with AlCl4−occurred mainly on C(sp3) atom.
AB - The mechanism of Cl-F exchange of halogenated cyclopentene with AlCl3in dimethylformamide (DMF) or with AlCl4−in 1,1,1,3,3-pentachloropropane (HCC-240fa) was investigated. It was found that in DMF, AlCl3preferred to attack the position with larger electron cloud density relatively like C(sp2) position, which was attributed to that AlCl3was a strong Lewis acid, and in HCC-240fa, AlCl4−preferred to attack the position with smaller electron cloud density relatively like C(sp3) position, which was attributed to that AlCl4−was a Lewis base. Our experimental results showed that Cl-F exchange with AlCl3occurred mainly on C(sp2) atom, and Cl-F exchange with AlCl4−occurred mainly on C(sp3) atom.
KW - AlCl
KW - AlCl
KW - Cl-F exchange
KW - Halogenated cyclopentene
KW - Lewis acid
UR - http://www.scopus.com/inward/record.url?scp=84989847646&partnerID=8YFLogxK
U2 - 10.1016/j.jfluchem.2016.09.011
DO - 10.1016/j.jfluchem.2016.09.011
M3 - Article
AN - SCOPUS:84989847646
SN - 0022-1139
VL - 191
SP - 84
EP - 89
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
ER -