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Undergoes many interesting transannular reactions to give bicyclic derivatives. Reaction with chloroform under free-radical conditions gives 2-(trichloromethyl)bicyclo[3.3.0]octane: Org. Synth. Coll., 5, 93 (1973); J. Am. Chem. Soc., 86, 946, 1885 (1964); Tetrahedron, 20, 1843 (1964). With Iodosobenzene diacetate, B24531, gives 2,6-diacetoxybicyclo[3.3.0]octane: Org. Synth. Coll., 8, 43 (1993). Addition of borane gives the important hydroborating agent 9-borabicyclo[3.3.1]nonane (9-BBN): J. Am. Chem. Soc., 90, 5280, 5281 (1968); J. Org. Chem., 46, 3978, 4599 (1981). Sulfur dichloride gives 2,6-dichloro-9-thiabicyclo[3.3.1]nonane: J. Org. Chem., 31, 1663, 1669 (1966); Org. Synth. Coll., 9, 692 (1998)./n
Allylic monobromination (NBS) followed by dehydrobromination gives 1,3,5-cyclooctatriene: Org. Synth. Coll., 9, 191 (1998). Addition of elemental bromine to the diene double bonds followed by dehydrobromination of the resulting tetrabromides with KO-t-Bu/ 18-crown-6 in THF gives the highly-reactive 1,5-cyclooctadiiyne. On prolonged base treatment, or in DMSO, conversion to cyclooctatetraene occurs: Chem. Ber., 127, 1529 (1994)./n
Useful bidentate ligand in transition metal chemistry. For examples, see Chloro(1,5-cyclooctadiene)iridium(I) dimer, 12749 and Chloro(1,5-cyclooctadiene)rhodium(I) dimer, 10466./n
Gefahrenhinweise (EU): H226-H302-H332-H315-H319-H317-H335
Flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction. May cause respiratory irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.