Synthesis of new acenaphthylene functional derivatives. 1. 1-(Trimethylsilyl)- and 1,2- and 1,5-bis(trimethylsilyl)acenaphthylenes and related compounds

✍ Scribed by Laguerre, Michel; Felix, Guy; Dunogues, Jacques; Calas, Raymond

• Book ID: 127310949
• Publisher: American Chemical Society
• Year: 1979
• Tongue: English
• Weight: 531 KB
• Volume: 44
• Category: Article
• ISSN: 0022-3263
• DOI: 10.1021/jo01338a012

✦ Synopsis

0.75 g, 15 mmol) and chlorotrimethylsilane (3.15 mL, 25 mmol) in dry acetonitrile (25 mL). The progress of the reactions was monitored by IR, and they were complete in 6-8 h. Pure silyl nitronates were obtained after workup and characterized by their NMR and IR spectra. Silyl nitronate of 6a: 1.0 g (98%); bp 37 °C (0.8 torr); IR 1635 cm"1 Uc-N); NMR (CDC13) 0.32 (s, 9 ), 1.74 (m, 6 H), 2.5 (dt, 4 H).

Silyl nitronate of 6b: 0.85 g (77%); bp 46 °C (0.6 torr); IR 1637 cm"1 Uc=n); NMR (CDC13) 0.46 (s, 9 ), 1.62-3.02 (m, 8 H), 4.52 and 5.3 (br d, 1 H).