Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement

Thibault Gendron, Raul Pereira, Hafsa Y. Abdi, Timothy H. Witney* and Erik Årstad*

*University College London, 72 Huntley Street, London WC1E 6DD; University College London, 20 Gordon Street, London WC1H 0AJ, United Kingdom, Email: tim.witneykcl.ac.uk, e.arstaducl.ac.uk

T. Gendron, R. Pereira, H. Y. Abdi, T. H. Witney, E. Årstadt, Org. Lett., 2020, 22, 249-252.

DOI: 10.1021/acs.orglett.9b04280

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Abstract

Iron(II)/ammonium persulfate in aqueous acetonitrile mediates a rapid Newman-Kwart rearrangement of electron-rich O-aryl carbamothioates under moderate heating to afford the rearranged products in excellent yields.

see article for more examples

proposed mechanism

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Key Words

Newman-Kwart Rearrangement

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ID: J54-Y2020