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ICl-Mediated Functional Group Interconversion from Methyl Homopropargyl Ether to α-Iodo-γ-chloroketone.

ABSTRACT: An ICl-mediated highly chemo- and regioselective functional group interconversion from methyl homopropargyl ether to α-iodo-γ-chloro-ketone is reported. Density functional theory (DFT)-calculated reaction coordinate and potential energy surface support the high chemo-selectivity observed for the formation of α-iodo-γ-chloroketone over furan. The five-membered oxonium ring formation-ring opening mechanism is a potential template for the preparation of polyfunctionalized carbonyl compounds.

SUBMITTER: Chen Y

PROVIDER: S-EPMC10174042 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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ICl-Mediated Functional Group Interconversion from Methyl Homopropargyl Ether to α-Iodo-γ-chloroketone.

Chen Yu Y Hee Samual S Liu Xiaochen X Das Sajal S Hong Dongsub D Leung Pak-Hing PH Li Yongxin Y Li Jiaming J Liu Jianbo J

The Journal of organic chemistry 20221104 22

An ICl-mediated highly chemo- and regioselective functional group interconversion from methyl homopropargyl ether to α-iodo-γ-chloro-ketone is reported. Density functional theory (DFT)-calculated reaction coordinate and potential energy surface support the high chemo-selectivity observed for the formation of α-iodo-γ-chloroketone over furan. The five-membered oxonium ring formation-ring opening mechanism is a potential template for the preparation of polyfunctionalized carbonyl compounds. ...[more]

PMID: 36331559

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