Gon-Ann Lee, Jay Chen, Chi-Sheng Chen
Jun 1, 1996
Citations
0
Influential Citations
6
Citations
Journal
Journal of The Chinese Chemical Society
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.