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Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis

Andrew J. Perkowski, Cole L. Cruz and David A. Nicewicz*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States, Email: nicewiczunc.edu

A. J. Perkowski, C. L. Cruz, D. A. Nicewicz, J. Am. Chem. Soc., 2015, 137, 15684-15687.

DOI: 10.1021/jacs.5b11800 (free Supporting Information)


Abstract

The high thermal conditions required for the Newman-Kwart rearrangement often leads to decomposition. A commercially available organic single-electron photooxidant catalyzes the rearrangement of O-aryl carbamothioates to S-aryl carbamothioates at ambient temperatures.

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Key Words

Newman-Kwart Rearrangement


ID: J48-Y2015