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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
Hazard Statements: 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.
Precautionary Statements: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a
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.