TY - JOUR
T1 - Electrolytic partial fluorination of organic compounds. 77. Reactivity of anodically generated benzylic cation intermediates toward fluoride ions in acetonitrile
AU - Tajima, Toshiki
AU - Kurihara, Hitoshi
AU - Nakajima, Atsushi
AU - Fuchigami, Toshio
PY - 2005/6/15
Y1 - 2005/6/15
N2 - Anodic benzylic fluorination of alkylbenzenes was comparatively studied in MeCN using Et4NF-4HF as a supporting electrolyte and a fluorine source. The anodic benzylic fluorination proceeded except for some cumene derivatives and the yields of fluorinated products greatly depended on the stability of the benzylic cation intermediates. It was found that fluoride ions reacted with more stable benzylic cations preferentially, while acetamidation took place preferentially at less stable benzylic cations.
AB - Anodic benzylic fluorination of alkylbenzenes was comparatively studied in MeCN using Et4NF-4HF as a supporting electrolyte and a fluorine source. The anodic benzylic fluorination proceeded except for some cumene derivatives and the yields of fluorinated products greatly depended on the stability of the benzylic cation intermediates. It was found that fluoride ions reacted with more stable benzylic cations preferentially, while acetamidation took place preferentially at less stable benzylic cations.
KW - Anodic benzylic fluorination
KW - Electrochemical fluorination
KW - Hammett's substituent constant
KW - Stability of benzylic cation
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U2 - 10.1016/j.jelechem.2005.03.024
DO - 10.1016/j.jelechem.2005.03.024
M3 - Article
AN - SCOPUS:18444415474
VL - 580
SP - 155
EP - 160
JO - Journal of Electroanalytical Chemistry
JF - Journal of Electroanalytical Chemistry
SN - 0022-0728
IS - 1
ER -