PREPARATION OF 1,5-CYCLOOCTADIYNE AND 1,3 ,5,7-CYCLOOCTATETRAENE FROM1,5-CYCLOOCTADIENE

Authors
DETERT H ROSE B MAYER W MEIER H
Citation
H. Detert et al., PREPARATION OF 1,5-CYCLOOCTADIYNE AND 1,3 ,5,7-CYCLOOCTATETRAENE FROM1,5-CYCLOOCTADIENE, Chemische Berichte, 127(8), 1994, pp. 1529-1532
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Chemische Berichte → ACNP
ISSN journal
00092940
Volume
127
Issue
8
Year of publication
1994
Pages
1529 - 1532
Database
ISI
SICI code
0009-2940(1994)127:8<1529:PO1A1,>2.0.ZU;2-F
Abstract
Bromination of 1,5-cyclooctadiene (1) and stepwise dehydrobromination first with KOtBu and then with KOtBu/18-crown-6 yields 1,5-cyclooctadi yne (5). A prolonged interaction of the base causes a complete transfo rmation to cyclooctatetraene (6). Diyne 5 and even more the intermedia te enyne 4 are highly reactive dienophiles. The cycloadducts 10-14 for med with 1,3-cyclohexadiene, carbon disulfide, and tetraphenylcyclopen tadienone were isolated and characterized. Treatment of 5 with titaniu m tetrachloride induces a vigorous polymerization.