Herstellung von 1,5-Cyclooctadiin und 1,3,5,7-Cyclooctatetraen aus 1,5-Cyclooctadien

✍ Scribed by Detert, Heiner ;Rose, Bernd ;Mayer, Winfried ;Meier, Herbert

• Publisher: Wiley (John Wiley & Sons)
• Year: 1994
• Tongue: English
• Weight: 444 KB
• Volume: 127
• Category: Article
• ISSN: 0009-2940
• DOI: 10.1002/cber.19941270829

✦ Synopsis

Bromination of 1,5-cyclooctadiene (1) and stepwise dehydro-enyne 4 are highly reactive dienophiles. The cycloadducts bromination first with KOtBu and then with KOtBu/l8-10-14 formed with 1,3-cyclohexadiene, carbon disulfide, crown-6 yields 1,5-~yclooctadiyne (5). A prolonged interac-and tetraphenylcyclopentadienone were isolated and charaction of the base causes a complete transformation to cyclooc-terized. Treatment of 5 with titanium tetrachloride induces a tatetraene (6). Diyne 5 and even more the intermediate vigorous polymerization.