Synfacts 2007(5): 0530-0530  
DOI: 10.1055/s-2007-968432
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Cyclic Oximes via Radical Ring Closure

Contributor(s): Paul Knochel, Tobias Thaler
D. L. J. Clive*, M. P. Pham, R. Subedi
University of Alberta, Edmonton, Canada
Further Information

Publication History

Publication Date:
24 April 2007 (online)

Significance

Radical carbocyclization reactions were successfully performed on O-trityl oximes using diphenyldiselenide (Ph2Se2) as key factor. The trityl leaving group is hereby assumed to become a persistent radical which aborts the course of the reaction. In the presence of minor amounts of Ph2Se2, PhSeH is formed on reaction with Bu3SnH. PhSeH is a much more efficient hydrogen donor than Bu3SnH and is capable of trapping the trityl radical, thus reinitiating the radical process.