Electrochemically Controlling the Ring Size and Molecular Topology of Cyclic Polyesters

Abstract

Five coordinated iron-bis(dithiolene) N-Heterocyclic carbene adducts [Fe(NHC)(S2C2R2)2] (R = phenyl or anisyl; NHC = 1,3-bis(2,4,6-trimethylphenyl)imida-zol-2-ylidene or 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)] has been isolated by reaction of [[Fe (S2C2R2)2] 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.

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Document Details

Document Type
Technical Report
Publication Date
May 01, 2017
Accession Number
AD1058708

Entities

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  • Kuppuswamy Arumugam

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  • Wright State University

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  • Chemistry

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