Electrochemically Controlling the Ring Size and Molecular Topology of Cyclic Polyesters
Technical Report,01 May 2016,31 Jan 2017
Wright State University Dayton United States
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Five coordinated iron-bisdithiolene N-Heterocyclic carbene adducts FeNHCS2C2R22 R phenyl or anisyl NHC 1,3-bis2,4,6-trimethylphenylimida-zol-2-ylidene or 1,3-Bis2,4,6-trimethylphenyl-4,5-dihydroimidazol-2-ylidene has been isolated by reaction of Fe S2C2R22 with the corresponding free carbenes. The synthesized adducts 1-4 were unambiguously confirmed by NMR and single crystal X-ray crystallography. All compounds 1-4 were characterized by electrochemistry and it displayed a reversible and an irreversible reduction coupled with a reversible peak in the oxidizing direction. Spectroelectrochemistry analysis of the complexes reveals that the irreversible reduction of compounds 1-4 readily release free N-heterocyclic carbene. Subsequently, electro-generated free NHC catalyzed organic transformation was validated with synthesis of gamma-butyrolactone from trans-cinnamaldehyde.
- Physical Chemistry
- Organic Chemistry