Electrolytic partial fluorination of organic compounds. 77. Reactivity of anodically generated benzylic cation intermediates toward fluoride ions in acetonitrile

Toshiki Tajima; Hitoshi Kurihara; Atsushi Nakajima; Toshio Fuchigami

doi:10.1016/j.jelechem.2005.03.024

Electrolytic partial fluorination of organic compounds. 77. Reactivity of anodically generated benzylic cation intermediates toward fluoride ions in acetonitrile

Toshiki Tajima, Hitoshi Kurihara, Atsushi Nakajima, Toshio Fuchigami

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	155-160
Number of pages	6
Journal	Journal of Electroanalytical Chemistry
Volume	580
Issue number	1
DOIs	https://doi.org/10.1016/j.jelechem.2005.03.024
Publication status	Published - 2005 Jun 15
Externally published	Yes

Keywords

Anodic benzylic fluorination
Electrochemical fluorination
Hammett's substituent constant
Stability of benzylic cation

ASJC Scopus subject areas

Analytical Chemistry
Chemical Engineering(all)
Electrochemistry

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10.1016/j.jelechem.2005.03.024

Cite this

Electrolytic partial fluorination of organic compounds. 77. Reactivity of anodically generated benzylic cation intermediates toward fluoride ions in acetonitrile. / Tajima, Toshiki; Kurihara, Hitoshi; Nakajima, Atsushi et al.
In: Journal of Electroanalytical Chemistry, Vol. 580, No. 1, 15.06.2005, p. 155-160.

Research output: Contribution to journal › Article › peer-review

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AU - Fuchigami, Toshio

PY - 2005/6/15

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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.

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KW - Electrochemical fluorination

KW - Hammett's substituent constant

KW - Stability of benzylic cation

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Electrolytic partial fluorination of organic compounds. 77. Reactivity of anodically generated benzylic cation intermediates toward fluoride ions in acetonitrile

Abstract

Keywords

ASJC Scopus subject areas

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