6533b82dfe1ef96bd12911c8
RESEARCH PRODUCT
Herstellung von 1,5‐Cyclooctadiin und 1,3,5,7‐Cyclooctatetraen aus 1,5‐Cyclooctadien
Winfried MayerHerbert MeierHeiner DetertBernd Rosesubject
Inorganic Chemistrychemistry.chemical_compoundCarbon disulfidePolymerizationEnynechemistryTetraphenylcyclopentadienoneDehydrohalogenationTitanium tetrachlorideHalogenationOrganic chemistryMedicinal chemistryCycloadditiondescription
Preparation of 1,5-Cyclooctadiyne and 1,3,5,7-Cyclooctatetraene from 1,5-Cyclooctadiene Bromination of 1,5-cyclooctadiene (1) and stepwise dehydro-bromination 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 cyclooc-tatetraene (6). Diyne 5 and even more the intermediate enyne 4 are highly reactive dienophiles. The cycloadducts 10–14 formed with 1,3-cyclohexadiene, carbon disulfide, and tetraphenylcyclopentadienone were isolated and characterized. Treatment of 5 with titanium tetrachloride induces a vigorous polymerization.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1994-08-01 | Chemische Berichte |