Formation of Highly Stable 1,2-Dicarbonyl Organic Radicals from Cyclic (Alkyl)(amino)carbenes

Formation of Highly Stable 1,2-Dicarbonyl Organic Radicals from Cyclic (Alkyl)(amino)carbenes

Two air-stable organic radicals derived from oxalyl chloride and cAAC were synthesized, resulting in the unexpected formation of a known (amino)­(carboxy) radical cation ([2]­BF4) and the oxidative formation of a 1,2-dicarbonyl radical cation ([3]­BF4) from a neutral 3-oxetanone compound (4). The hi...

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Veröffentlicht in:Organic letters 2023-06, Vol.25 (23), p.4292-4297
Hauptverfasser: Choe, Solhye, Song, Hayoung, Choi, Hyeonjeong, Yoo, Seunghyuk, Kim, Jaelim, Ko, Young Ho, Lee, Eunsung
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container_end_page 4297
container_issue 23
container_start_page 4292
container_title Organic letters
container_volume 25
creator Choe, Solhye
Song, Hayoung
Choi, Hyeonjeong
Yoo, Seunghyuk
Kim, Jaelim
Ko, Young Ho
Lee, Eunsung
description Two air-stable organic radicals derived from oxalyl chloride and cAAC were synthesized, resulting in the unexpected formation of a known (amino)­(carboxy) radical cation ([2]­BF4) and the oxidative formation of a 1,2-dicarbonyl radical cation ([3]­BF4) from a neutral 3-oxetanone compound (4). The highly strained and newly discovered 4 was obtained by a single-electron reduction of [3]­BF4 with a mild reducing agent. This result differs from the generation of NHC-based 1,2-dicarbonyl radicals, indicating the uniqueness of cAAC.
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title Formation of Highly Stable 1,2-Dicarbonyl Organic Radicals from Cyclic (Alkyl)(amino)carbenes
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