Download PDF
Synfacts 2006(4): 0407-0407  
DOI: 10.1055/s-2006-932091
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Photooxygenation Using ROM Polymer Sphere-Supported seco-Porphyrazines

Contributor(s): Yasuhiro Uozumi, Masahiro Kimura
M. J. Fuchter, B. M. Hoffman*, A. G. M. Barrett*
Imperial College London, UK and Northwestern University, USA
Further Information

Publication History

Publication Date:
24 March 2006 (online)

    Permissions and Reprints

Significance

A novel ring-opening metathesis polymer (ROMP) sphere-supported seco-porphyrazine 3 was developed. The ROMPsphere ­reagent 3 was prepared by copolymerization of seco-porphyrazine 1 with norbornene in the presence of the Merrifield resin supported ruthenium catalyst 2 in refluxing dichloromethane. Catalyst 3 was used for the [4+2] cycloaddition of singlet oxygen to 1,3-dienes. Thus, for example, the reaction of α-terpinene (4) with oxygen by irradiation with a 40 W desk lamp in the presence of 1 mol% catalyst 3 gave pure ascaridole (5) in 97% isolated yield.