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J Org Chem. 2015 Feb 20;80(4):2418-24. doi: 10.1021/jo502605e. Epub 2015 Feb 03.

Synthesis and properties of arylvinylidene-bridged triphenylamines.

The Journal of organic chemistry

Natalie Hammer, Tatyana E Shubina, Jean-Paul Gisselbrecht, Frank Hampel, Milan Kivala

Affiliations

  1. Lehrstuhl für Organische Chemie I, Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg , Henkestrasse 42, D-91054 Erlangen, Germany.

PMID: 25603313 DOI: 10.1021/jo502605e

Abstract

A series of arylvinylidene-bridged triphenylamines were efficiently synthesized through the thionation/Barton-Kellogg olefination sequence from their corresponding carbonyl precursors. The electrochemical investigations identified these highly distorted scaffolds as fairly strong electron donors capable of several reversible oxidation steps with the first oxidation occurring at a potential comparable to that of ferrocene for the n-hexyl-substituted diphenylvinylidene-bridged compound.

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