Nickel-Catalyzed Cyclodimerization of 2-tert-Butyl- and 2-Trimethylsilyl-1,3-butadiene

✍ Scribed by Dr. Tamas Bartik; Prof. Paul Heimbach; Dipl.-Chem. Thomas Himmler; Dr. Richard Mynott

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: English
• Weight: 220 KB
• Volume: 24
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198503131

✦ Synopsis

161 16 g Al powder, suspended in 500 mL n-heptane, was treated for 4 d with C :Hr ( I bar) after addition of 30 g AICI, with stirring at 100°C. The mixture was filtered and the filtrate freed of solvent (maximum 50°C. 10mbar). The oily residue (17.75 g) was treated with pentane. A colorless powder precipitated out (24.14°/0 Al, 63.32% CI, 12.32% ethane; deuterolysis: 95% [ I,l-DZ]ethane, 5% [DJethane). The structure of 2 shown here is in accord with the 'H-NMR spectrum (230K) (rC(C'-H)= -l.20,S(CH3)=0.92) as wellas with the "C-NMRspectrum (210 K) (6(C-H= 1.95 (d), 6(CHi)=5.71 ( )). The solid residue from the filtered reaction mixture contains undissolved 1 in addition to excess Al powder.0 I'CH Verlag~gesellsrliafr mbH. 0.6940 Wernheim. 1985