Oxidative cyclorelease from soluble polymeric supports.
[reaction: see text] Single electron oxidation is shown to be a viable method for effecting concomitant cyclization and cleavage (cyclorelease) of a series of polymer bound homobenzylic ethers. Soluble oligonorbornene polymers are stable toward redox chemistry and are isolable through precipitation with methanol, making them excellent supports for this process. These oxidative conditions are also shown to cleave secondary and tertiary alcohols and ethers in a new traceless approach to polymer-supported aldehyde and ketone synthesis.
Liu
Hua
H
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Wan
Shuangyi
S
Floreancig
Paul E
PE