UV and ESR Studies of p-Bis(trimethylsilyl)- and p-Dialkylbenzenes

✍ Scribed by Dipl.-Chem. H. Alt; Priv.-Doz. Dr. H. Bock; Priv.-Doz. Dr. F. Gerson; Dipl.-Chem. J. Heinzer

• Publisher: John Wiley and Sons
• Year: 1967
• Tongue: English
• Weight: 238 KB
• Volume: 6
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196709412

✦ Synopsis

The 19F-NMR spectrum at 30 "C contains one very broad signal, which becomes narrower with decrease in the temperature. At -60°C the chemical shift amounts to -55.1 ppm referred to CC13F as internal standard. The mass spectrum of (3) contains the typical fragments SC-NCS ( m / e = 102), CNCS (70), SCF (63), CS (44), and F C (31), as well as the molecule ion at m/e = 121. An equimolar mixture of (3) and chlorine reacts at -70 "C in a bomb tube in an extremely short time, the color becoming paler and the chlorine being consumed quantitatively. Elemental analysis and the IR, 19F-NMR, and mass spectra of the yellow liquid product showed that FCI(SCN)C-SCI ( 4 ) is formed quantitatively in this reaction; this compound boils at 53 "CjlO mm and has the typical odor of sulfenyl chlorides. The IR spectrum contains a strong absorption band at 1958 cm-1 and bands of medium strength at 530, 575, 811, 1040, and 1165cm-1. The 19F-NMR spectrum of (4) at 3OoC contains a single signal with chemical shift +44.7 ppm referred to CC13F as internal standard. The mass spectrum shows, inter aliu, fragments FCl(S)C-NCS ( m / e = 156), FClC-NCS (124), F(S)C-NCS (121), and SCClF (98).