Zhong Long-Jin, Fan Jian-Hong, Chen Pu, Huang Peng-Fei, Xiong Bi-Quan, Tang Ke-Wen, Liu Yu
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
Org Biomol Chem. 2023 Dec 20;22(1):10-24. doi: 10.1039/d3ob01762a.
Cyclobutanone oximes and their derivatives are pivotal core structural motifs in organic chemistry. Iminyl-radical-triggered C-C bond cleavage of cyclobutanone oximes delivers an efficient strategy to produce stable distal cyano-substituted alkyl radicals, which can capture SO, CO or O to form cyanoalkylsulfonyl radicals, cyanoalkylcarbonyl radicals or cyanoalkoxyl radicals under mild conditions. In the past several years, cyanoalkylsulfonylation/cyanoalkylcarbonyaltion/cyanoalkoxylation has attracted a lot of interest. In this updated report, the strategies for trapping SO, CO or O iminyl-radical-triggered ring-opening of cyclobutanone oximes are summarized.
环丁酮肟及其衍生物是有机化学中关键的核心结构基序。环丁酮肟的亚胺基自由基引发的C-C键裂解提供了一种高效策略，可生成稳定的远端氰基取代烷基自由基，该自由基在温和条件下能捕获SO、CO或O，形成氰基烷基磺酰基自由基、氰基烷基羰基自由基或氰基烷氧基自由基。在过去几年中，氰基烷基磺酰化/氰基烷基羰基化/氰基烷氧基化引起了广泛关注。在这份更新报告中，总结了捕获由亚胺基自由基引发的环丁酮肟开环所产生的SO、CO或O的策略。
