49852-40-6Relevant articles and documents
Preparation of 1,5-Cyclooctadiyne and 1,3,5,7-Cylooctatetraene from 1,5-Cyclooctadiene
Detert, Heiner,Rose, Bernd,Mayer, Winfried,Meier, Herbert
, p. 1529 - 1532 (2007/10/02)
Bromination of 1,5-cyclooctadiene (1) and stepwise dehydrobromination first with KOtBu and then with KOtBu/18-crown-6 yields 1,5-cyclooctadiyne (5).A prolonged interaction of the base causes a complete transformation to cyclooctatetraene (6).Diyne 5 and even more the intermediate enyne 4 are highly reactive dienophiles.The cycloadducts 10-14 formed with 1,3-cyclohexadiene, carbon disulphide, and tetraphenylcyclopentadienone were isolated and characterized.Treatment of 5 with titanium tetrachloride induces a vigorous polymerization. - Key Words: Cycloalkynes / Dehydrohalogenation / Cycloaddition