Electrochemistry
Online ISSN : 2186-2451
Print ISSN : 1344-3542
ISSN-L : 1344-3542
Communications
Electro-Generated Acids Catalyzed Epoxyolefin Cyclizations via Cationic Chain Reactions
Kouichi MATSUMOTOHiroki SHIMAOYuta FUJIKINorihito KAWASHITAShigenori KASHIMURA
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2020 年 88 巻 4 号 p. 262-264

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We show that a catalytic amount of electro-generated acid (EGA) prepared from the oxidation of a Bu4NB(C6F5)4/CH2Cl2 solution catalyzes effectively the tandem cyclization of epoxyolefins, producing the corresponding polycyclized compounds in 23%–57% yields. The scope and limitations of the substrates are examined, and we compare the stability of the intermediates through theoretical calculations. The success of the current reactions might be due to the high reactivity of EGA, because the counter anion is bulky and stabilized B(C6F5)4 derived from Bu4NB(C6F5)4 as the supporting electrolyte.

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© The Author(s) 2020. Published by ECSJ.

This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 License (CC BY, http://creativecommons.org/licenses/by/4.0/), which permits unrestricted reuse of the work in any medium provided the original work is properly cited. [DOI: 10.5796/electrochemistry.20-00032].
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