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Issue 15, 2018
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Direct dihalo-alkoxylation of nitroalkenes leading to β,β-dihalo-β-nitroethyl alkyl ethers

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Abstract

A highly efficient one-pot synthesis of β,β-dihalo-β-nitroethyl alkyl ethers is achieved by the treatment of nitroalkenes with alcohols and N-halosuccinimides in the presence of sodium hydride. The notable advantages of this protocol are that it involves simple experimental manipulations and tolerates a wide range of functional groups. Further transformations of the obtained ethers, such as allylation and conversion to β,β-dihalogenated vinyl ethers, are also investigated.

Graphical abstract: Direct dihalo-alkoxylation of nitroalkenes leading to β,β-dihalo-β-nitroethyl alkyl ethers

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Publication details

The article was received on 15 Feb 2018, accepted on 23 Mar 2018 and first published on 23 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00408K
Citation: Org. Biomol. Chem., 2018,16, 2768-2775
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    Direct dihalo-alkoxylation of nitroalkenes leading to β,β-dihalo-β-nitroethyl alkyl ethers

    F. Hao, S. Yokoyama and N. Nishiwaki, Org. Biomol. Chem., 2018, 16, 2768
    DOI: 10.1039/C8OB00408K

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