Reactions of monoaryl-substituted methylenecyclobutanes and methylenecyclopropanes with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu).
Monoaryl-substituted methylenecyclobutanes (MCBs) and methylenecyclopropanes (MCPs) react with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu) smoothly to produce the corresponding cyclobutylmethanone and cyclopropylmethanone derivatives 2, 4, and 5 via a cascade epoxidation and nucleophilic addition process or the corresponding epoxides 6 in moderate to good yields under mild conditions. A plausible mechanism has been proposed on the basis of the control experiments and the isolation of the reaction intermediates.
Jiang
Min
M
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China.
Shi
Min
M
D001372:Aza Compounds / Q000737:chemistry*; D003503:Cyclobutanes / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis; D007659:Ketones / Q000138:chemical synthesis; D013388:Succinimides / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D001372:Aza Compounds; D003503:Cyclobutanes; D003521:Cyclopropanes; D004852:Epoxy Compounds; D007659:Ketones; D013388:Succinimides; D014230:Triazoles; C508672:methylenecyclopropane; C011852:1-hydroxybenzotriazole; C001426:N-hydroxysuccinimide; C435757:1-hydroxy-7-azabenzotriazole