- Synthesis, Structure, and Properties of Amino-Substituted Benzhydrylium Ions – A Link between Ordinary Carbocations and Neutral Electrophiles
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Optimized synthetic procedures for the straightforward access to eleven amino-substituted diarylmethylium tetrafluoroborates are described. These benzhydrylium ions cover a range of seven orders of magnitude in electrophilicity and provide a link between ordinary carbocations and neutral electrophiles. Five of these highly stabilized benzhydrylium tetrafluoroborates were characterized by single-crystal X-ray crystallography. While the experimentally determined bond lengths and angles in the solid state perfectly agree with those calculated by DFT methods for the gas phase and aqueous solution, crystal packing accounts for large differences in the twist angles of the aryl groups found in the solid state as compared to calculated structures.
- Mayer, Robert J.,Hampel, Nathalie,Mayer, Peter,Ofial, Armin R.,Mayr, Herbert
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supporting information
p. 412 - 421
(2018/09/14)
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- New tetrakis(4-aminophenyl)ethenes: Synthesis and electrochemical investigations
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Four novel functional conjugated tetraarylamines containing a tetraphenylenecore were synthesized via Ni-catalyzed aryl amination followed by McMurry olefination. Their electrochemical properties were studied by cyclic voltammetry, coulometry, and electro
- Kuntz, Jean-Fran?ois,Schneider, Rapha?l,Walcarius, Alain,Fort, Yves
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p. 8793 - 8797
(2007/10/03)
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- Nickel(0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines
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A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.
- Desmarets, Christophe,Schneider, Raphael,Fort, Yves
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p. 3029 - 3036
(2007/10/03)
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- Solid-state structures of N-substituted Michler's ketones and their relation to solvatochromism
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The solvatochromism (vmax) of N-substituted Michler's ketones - including 4′-[bis(2-acetoxyethyl)amino]-4-(dimethylamino)benzophenone [MK(OAc)2, 1a], 4,4′-bis(diethylamino)benzophenone [MK(NEt2)2, 1e], 4,4′-bis(
- Spange, Stefan,El-Sayed, Mohamed,Mueller, Hardy,Rheinwald, Gerd,Lang, Heinrich,Poppitz, Wolfgang
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p. 4159 - 4168
(2007/10/03)
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- The effects of cyclic terminal groups on the electronic absorption spectra of di- and tri-phenylmethane dyes
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The spectral shifts of the first absorption bands brought about by cyclic terminal groups in analogues of Michler's Hydrol Blue, Malachite Green, and Crystal Violet are determined mainly by inductive effects.Dye cations containing terminal pyrrolidino substituents are significantly more stable than those possessing piperidino groups as a result of differences in basicity brought about by a change in size of the saturated heterocyclic ring.
- Beach, Steven F.,Hepworth, John D.,Jones, Peter,Mason, Donald,Sawyer, John,et al.
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p. 1087 - 1090
(2007/10/02)
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