Supporting Information © Wiley-VCH 2007 69451 Weinheim, Germany Development of a Novel Electrolytic System for Anodic Fluorination Based on Cation Exchange Reaction between Alkali Metal Fluorides and Solid-Supported Acids Toshiki Tajima,*, a Atsushi Nakajima,b Yuta Doi,b and Toshio Fuchigamib a Global Edge Institute, Tokyo Institute of Technology, Yokohama 226-8502, Japan b Department of Electronic Chemistry, Tokyo Institute of Technology, Yokohama 226- 8502, Japan E-mail:
[email protected] (T. Tajima) 1. General 1H, 13C, and 19F NMR spectra were recorded on JEOL JNM EX-270 (1H: 270 MHz, 13 19 1 13 C: 67.8 MHz, F: 254 MHz) spectrometer in CDCl3. The chemical shifts for H, C, 19 and F NMR spectra were given in d (ppm) from internal TMS, CDCl3, and monofluorobenzene (-36.5 ppm), respectively. EI mass spectra were measured with Shimadzu GCMS-QP5050A mass spectrometer. Preparative liquid chromatography was carried out using the following apparatuses: SHIMADZU LC-6AD (liquid chromatograph), SHIMADZU SPD-20A (UV detector), and SHIMADZU C-R8A (chromatopac). Cyclic voltammetry was performed by using a computer-controlled electrochemical analyzer (ALS/CH Instruments 610B), and preparative electrolyses were carried out with HOKUTO DENKO HABF-501 Potentiostat/Galvanostat. 2. Materials Ethyl a-phenylthioacetate (1), 4,4’-diisopropylbiphenyl (7), and 2,6-lutidine were purchased from Tokyo Chemical Industry and used without purification. Phenylthioacetonitrile (3) and triethylamine were purchased from Wako Pure Chemical Industries and used without purification. 4-Isopropyl-3,4-dihydro-2H-1,4-benzothiazin- 3-one (5) was synthesized according to the literature.[1] Dehydrated acetonitrile was purchased from Kanto Chemical.