157735-41-6Relevant academic research and scientific papers
Synthesis and crystallography of 8-halonaphthalene-1-carbonitriles and naphthalene-1,8-dicarbonitrile
Noland, Wayland E.,Narina, Venkata Srinivasarao,Britton, Doyle
, p. 694 - 697 (2011)
A convenient and high-yielding three-step synthesis of 8-halonaphthalene-1- carbonitriles has been achieved by ring opening of 1H-naphtho[1,8-de][1,2,3] triazine with the corresponding halides as the key step. Naphthalene-1,8- dicarbonitrile also has been synthesised from 8-bromonaphthalene-1-carbonitrile via palladium-catalysed cyanation of the aryl bromide. The crystal structures of 8-chloronaphthalene-1-carbonitrile, the A polymorph of the bromo analogue, and naphthalene-1,8-dicarbonitrile are isomorphous with orthorhombic symmetry. The B polymorph of the bromo compound and the iodo analogue are also isomorphous, but with monoclinic symmetry. In all of the halo carbonitriles, the molecules are disordered with respect to the location of the halogen atoms and the nitrile groups. There are no intermolecular X...NC interactions in any of the solids.
Palladium-catalyzed highly selective ortho-halogenation (I, Br, Cl) of arylnitriles via sp2 C-H bond activation using cyano as directing group
Du, Bingnan,Jiang, Xiaoqing,Sun, Peipei
, p. 2786 - 2791 (2013/04/24)
A palladium-catalyzed ortho-halogenation (I, Br, Cl) of arylnitrile is described. The optimal reaction conditions were identified after examining various factors such as catalyst, additive, solvent, and reaction temperature. Using cyano as the directing group, the halogenation reaction gave good to excellent yields. The method is compatible to the arylnitriles with either electron-withdrawing or electron-donating groups. The reaction is available to the substrate in at least gram scale. The present method was successfully applied to the synthesis of the precursors of paucifloral F and isopaucifloral F.
Enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted Diels?Alder reaction
Weimar, Marko,Duerner, Gerd,Bats, Jan W.,Goebel, Michael W.
supporting information; experimental part, p. 2718 - 2721 (2010/07/17)
Starting from Danes diene and methylcyclopentenedione, (+)-estrone is synthesized along the Quinkert?Dane route in 24% total yield. The key step is an enantioselective Diels?Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid.
Supramolecular Phosphoryl Transfer Reactions Mediated by Amidinium Phosphate Ion-Pair Complexes
Mueller, Gilbert,Duerner, Gerd,Bats, Jan W.,Goebel, Michael W.
, p. 1075 - 1092 (2007/10/02)
In order to build up simplified synthetic models of staphylococcal nuclease two derivatives of 8-phenylnaphthalene-1-carboxamidine equipped with nucleophilic side chains have been prepared (1, 2).After protonation these amidinium alcohols bind phosphodiester anions via hydrogen bonds and react within the ion-pair complexes to give zwitterionic products 27 and 28.The rate accelerations (DMF, 30 deg C) compared to the phosphorylation of noncharged alcohols are 2700-fold (2) and 930-fold (1). - Key Words: Artificial phosphodiesterase / Naphthalene, 1,8-disubstituted / Molecular Recognition / Staphylococcal nuclease, model of / Enzymes / Amidinium phosphate / Ion-Pair Complexes / Guanidine
