| Abstract: | 9-Chlorobicyclo[6.1.0]non-l(9)-ene ( 4 ), a 2-chlorinated 1,3-fused cyclopropene, is synthesized and isolated from the dehalogenation of the l-bromo-9,9-dichlorobicyclo[6.1.0]nonane, itself derived from cyclooctene. Compound 4 undergoes ring opening reaction to generate cyclooctenyl chlorocarbene ( 9 ) which reacts with water via conjugate addition and ipso-addition to give ( E )-2-(chloromethylene)cyclooctanol ( 7 ) and cyclooctene-l-carboxaldehyde ( 8 ), respectively. The conjugate addition of 9 with water is more favorable than the ipso-addition by 3:1. Compound 4 , which is stable at ?25 °C for weeks without any decomposition, reacts with oxygen to produce 2-chlorocyclonon-2-enone ( 12 ) via the ring-opening reaction adduct, vinyl alkylcarbene 10 . |
