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- You have full text access to this OnlineOpen articleDiastereoselective Additive Trifluoromethylation/Halogenation of Isoxazole Triflones: Synthesis of All-Carbon-Functionalized Trifluoromethyl Isoxazoline Triflones (pages 14–18)
Dr. Hiroyuki Kawai, Yutaka Sugita, Etsuko Tokunaga, Hiroyasu Sato, Dr. Motoo Shiro and Prof. Dr. Norio Shibata
Article first published online: 13 FEB 2014 | DOI: 10.1002/open.201300044
The SO2CF3 group acts three! Highly functionalized 5-trifluoromethyl-2-isoxazoline derivatives featuring a triflyl (SO2CF3) group at the 4-position were successfully synthesized via diastereoselective trifluoromethylation and halogenation of isoxazole triflones using the Ruppert–Prakash reagent. The triflyl group activates isoxazoles and the 4-position of CF3 adducts, and has a potential biological function.
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- You have full text access to this OnlineOpen articleUnderstanding E2 versus SN2 Competition under Acidic and Basic Conditions (pages 29–36)
Lando P. Wolters, Prof. Dr. Yi Ren and Prof. Dr. F. Matthias Bickelhaupt
Article first published online: 29 JAN 2014 | DOI: 10.1002/open.201300043
Titrating the LUMO: The character of the LUMO of a substrate CH3CH2−LG (LG=leaving group) is found to be pH dependent: whereas it is Cβ−H bonding under acidic conditions, it is Cβ−H antibonding under basic conditions. This is an important factor behind the corresponding shift in reactivity towards an electron-donating agent Nu from substitution to elimination.
- You have full text access to this OnlineOpen articleOne-Pot Synthesis and Applications of N-Heteroaryl Iodonium Salts (pages 19–22)
Dr. Marcin Bielawski, Joel Malmgren, Dr. Leticia M. Pardo, Ylva Wikmark and Prof. Berit Olofsson
Article first published online: 23 JAN 2014 | DOI: 10.1002/open.201300042
N-Heteroarylation: An efficient one-pot synthesis of N-heteroaryl iodonium triflates from the corresponding N-heteroaryl iodide has been developed. The reactivity and chemoselectivity of these iodonium salts were demonstrated by selectively introducing a pyridyl moiety onto both oxygen and carbon nucleophiles in good yields.
- You have full text access to this OnlineOpen articleDifluoro- and Trifluoromethylation of Electron-Deficient Alkenes in an Electrochemical Microreactor (pages 23–28)
Dr. Kenta Arai, Kevin Watts and Prof. Dr. Thomas Wirth
Article first published online: 26 NOV 2013 | DOI: 10.1002/open.201300039
In the flow! In an electrochemical microreactor, Kolbe electrolysis of acetic acid derivatives allows facile difluoro- and trifluoromethylation of electrondeficient alkenes. Compared with bulk reactions, higher yields are achieved at room temperature and in short reaction times.