Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Australian Journal of Chemistry

Australian Journal of Chemistry

Volume 70 Number 4 2017

7th Heron Island Conference

CH16587Syntheses, Structural Studies, and Copper Iodide Complexes of Macrocycles Derived from Williamson Ether Syntheses Involving 2,9-Bis(4-hydroxyphenyl)-1,10-phenanthroline, α,ω-Dibromides, and Resorcinol or 2,7-Dihydroxynaphthalene

Zuzana Baranová, Hashem Amini, Madhav Neupane, Sydney C. Garrett, Andreas Ehnbom, Nattamai Bhuvanesh, Joseph H. Reibenspies and John A. Gladysz
pp. 373-386
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The title macrocycles were assembled by first combining the grey and maroon building blocks, followed by a condensation with 1. The CuI moieties were markedly removed from the 1,10-phenanthroline planes, as represented by the basketball above the basket rim, and voids in the crystals were analyzed in the context of rotaxane formation.

CH16602Hydroxyl Radicals via Collision-Induced Dissociation of Trimethylammonium Benzyl Alcohols

Peter W. Moore, Jordan P. Hooker, Athanasios Zavras, George N. Khairallah, Elizabeth H. Krenske, Paul V. Bernhardt, Gina Quach, Evan G. Moore, Richard A. J. O'Hair and Craig M. Williams
pp. 397-406
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Arguably the most famous of all small molecule reactive intermediates is the hydroxyl radical. Methods to generate hydroxyl radicals from organic precursors are rare, with only one known example for the solution phase. Mass spectrometry is a key identifying technique is this area, and reported herein are new HO and DO radical precursors based on the trimethylammonium benzyl alcohol motif.

CH16622Nitrosonium-Mediated Phenol–Arene Cross-Coupling Involving Direct C–H Activation

Anna Eisenhofer, Uta Wille and Burkhard König
pp. 407-412
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An environmentally benign and mild method for the in situ formation of NO+ from readily available nitrate salts by treatment with formic acid and MeOH is described. The synthetic applicability of the method was demonstrated for the oxidative phenol–arene C–C cross-coupling by direct C–H activation.

CH16604Singlet Photoreactivity of 3-Methyl-2-phenyl-2H-azirine

Geethika K. Weragoda, Anushree Das, Sujan K. Sarkar, H. Dushanee M. Sriyarathne, Xiaoming Zhang, Bruce S. Ault and Anna D. Gudmundsdottir
pp. 413-420
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Laser flash photolysis of 3-methyl-2-phenyl-2H-azirine (1) in acetonitrile (irradiation wavelength = 266 nm) and in cryogenic argon matrices (irradiation wavelength = 254 nm) results in the corresponding ylide.

CH17026Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine

Sergei F. Vasilevsky, Maria P. Davydova, Victor I. Mamatyuk, Nikolay Tsvetkov, Audrey Hughes, Denis S. Baranov and Igor V. Alabugin
pp. 421-429
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This work uses the electronic and spatial features of alkynes, enhanced by conjugated electron acceptors, to achieve complete triple-bond fragmentation. Sonogashira coupling, then ethylenediamine-mediated triple-bond scission allows selective halogen substitution in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.

CH16580Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes

Ciputra Tejo, Davin Tirtorahardjo, David Philip Day, Dik-Lung Ma, Chung-Hang Leung and Philip Wai Hong Chan
pp. 430-435
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A Brønsted base-mediated method for the synthesis of α,α-diacylaziridines and α,α,β-triacylaziridines from reaction of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds with arylsulfonyliminoiodinanes (ArSO2N=IPh) under atmospheric conditions is described.

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An N-heterocyclic carbene catalysed Mukaiyama–Michael addition between several TMS enol ethers and chalcone derivatives has been discovered. Also the related dehydrative Mukaiyama aldol followed by a Mukaiyama–Michael addition process has been developed. The enantioselective variant of these reactions has been examined with homochiral catalysts, which are active but fail to achieve enantioinduction.

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A study on the acid-induced ring-expansion reaction of the first oxaphosphirane complex bearing C6F5 as an electron-withdrawing C-substituent using trifluoromethanesulfonic acid and electronically different aldehydes is described. The stereoselectively obtained 1,3,4-dioxaphospholane complexes 4ac were unambiguously characterized by elemental analysis, multinuclear NMR, mass spectrometry, and single crystal X-ray diffraction studies.

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