Synthesis of phenazine derivatives for use as precursors to electrochemically generated bases |
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Authors: | Mateo Alonso A Horcajada Roberto Groombridge Helen J Chudasama Née Mandalia Reshma Motevalli Majid Utley James H P Wyatt Peter B |
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Institution: | Department of Chemistry, Queen Mary, University of London, Mile End Road, London, UK E1 4NS. |
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Abstract: | 1,6-Disubstituted phenazine derivatives for use as precursors to electrochemically generated bases have been synthesized from readily available starting materials. Reaction of 1,6-dihydroxyphenazine with 1,10-diododecane, 1,11-diiodo-3,6,9-trioxaundecane or (R,R)-(-)-1,2-bis(3-iodopropoxy)cyclohexane gave planar chiral phenazinophanes containing ether-linked bridges; molecular structures of all these compounds have been determined by X-ray crystallography. Substituted 1,6-diaminophenazines were prepared by palladium-mediated amination of 1,6-dichlorophenazine and acylation of 1,6-diaminophenazine followed by reduction. Reaction of 1,6-bis(alkylamino)phenazines with sebacoyl chloride gave planar chiral phenazinophanes containing amide-linked bridges. |
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