On the electrochemical polymerization of acrylonitrile and n-vinylpyrrolidone: new insight into the mechanism

✍ Scribed by Prof. Robert Jérǒme; Marc Mertens; Dr. Lucien Martinot

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 319 KB
• Volume: 7
• Category: Article
• ISSN: 0935-9648
• DOI: 10.1002/adma.19950070911

✦ Synopsis

Communications 2-Fluoro-5-[trans-4-(fmns-4"-pentylcyclohexyl)-cyclohexyl]pyrimidine CCM-5-F: 2-Dimethylamino-5-[tru~,~-4'-(trun.~-4"-pentylcyclohexyl)-cyclohexyllpyrimidine (30.2 g, 85 mmol) was dissolved in 300 ml toluene and at 0 "C methyltrifluoromethylsulfonate (16.4 g, 100 mmol) in 40 ml of toluene was added. After the addition the mixture was allowed to warm to room temperature and the white precipitate was isolated by filtration and dried in vacuo to afford 40.1 g (90%) of white crystals. According to NMR, a 2: 1 mixture of ring-N and dimethylamino-N alkylated pyrimidines was formed but was used for the next step without purification.

In a second flask tetrabutylammonium fluoride trihydrate (34.5 g, 390 mmol) was dissolved in toluene and water was removed azeotropically in a Dean-Stark trap. The mixture of methylated dimethylaminopyrimidines (11 .O g, 21 mmol) was added at 80°C and stirred overnight at that temperature. Water was added and the organic phase was separated, dried, filtered and evaporated to give 17.3 g of a red-brown residue which was purified by flash chromatography (silica gel, tohenelethylacetate 8: 2) and finally recrystallized from hexane affording 370 mg ( 5 % ) of white crystals. 'H-NMR (200 MHz, CDCI,, TMS) 6 = 0.85-2.00 (br, 30H, aliphatic CH), 2.55 (m, 1H. benzylic CH), 8.45 (d. lH, pyrimidine CH). MS m/e = 333 (M +), 261, 192