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Switching the reaction pathways of electrochemically generated ?-haloalkoxysulfonium ions - synthesis of halohydrins and epoxides.

ABSTRACT: ?-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br(+) and I(+) ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave ?-halocarbonyl compounds.

SUBMITTER: Shimizu A

PROVIDER: S-EPMC4362321 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions - synthesis of halohydrins and epoxides.

Shimizu Akihiro A Hayashi Ryutaro R Ashikari Yosuke Y Nokami Toshiki T Yoshida Jun-Ichi J

Beilstein journal of organic chemistry 20150213

β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br(+) and I(+) ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds. ...[more]

PMID: 25815076

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