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. Author manuscript; available in PMC: 2019 Mar 11.
Published in final edited form as: J Am Chem Soc. 2018 Oct 19;140(43):13988–14009. doi: 10.1021/jacs.8b05195

Figure 18.

Figure 18.

Fe(PDP) discriminates between aliphatic C–H bonds on the basis of their stereoelectronic properties. (A) Oxygen functionality hyperconjugatively activates adjacent methylene sites to furnish preparative yields of mono-oxidized products with Fe(PDP) oxidations and light-promoted radical xanthylation. (B,C) Cyclopropane rings that act as hyperconjugative activators in Fe(PDP) catalysis are opened with radical reagents. (D) Ring-strain release (release of torsional strain) promotes oxidation at C3 of substituted cyclohexane rings with Fe(PDP) catalysis.