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Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement.


ABSTRACT: Herein, we report that iron(II)/ammonium persulfate in aqueous acetonitrile mediates the Newman-Kwart rearrangement of O-aryl carbamothioates. Electron-rich substrates react rapidly under moderate heating to afford the rearranged products in excellent yields. The mild conditions, rapid reaction rates, and suitability for scale up offers immediate practical benefits to access functionalized thiophenols.

SUBMITTER: Gendron T 

PROVIDER: S-EPMC6989215 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement.

Gendron Thibault T   Pereira Raul R   Abdi Hafsa Y HY   Witney Timothy H TH   Årstad Erik E  

Organic letters 20191218 1


Herein, we report that iron(II)/ammonium persulfate in aqueous acetonitrile mediates the Newman-Kwart rearrangement of <i>O</i>-aryl carbamothioates. Electron-rich substrates react rapidly under moderate heating to afford the rearranged products in excellent yields. The mild conditions, rapid reaction rates, and suitability for scale up offers immediate practical benefits to access functionalized thiophenols. ...[more]

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