title: Synthesis of an anti-Bredt compound, bicyclo[3.2.2]nona-1,6,8-triene, via the isomerization of tricyclo[3.2.2.0(2,4)]nona-2,6-diene.
abstract: A highly strained 1,3-fused tricyclic cyclopropene, tricyclo[3.2.2.0(2,4)]nona-2,6-diene (15), was designed for use in the synthesis of a new highly strained anti-Bredt compound, bicyclo[3.2.2]nona-1,6,8-triene (17). Tricyclic cyclopropene 15 was subjected to a ring-opening reaction followed by insertion of the resulting carbene to produce an anti-Bredt compound 17. The tricyclic cyclopropene 15 was prepared by the fluoride-induced elimination of 2-chloro-3-trimethylsilyltricyclo[3.2.2.0(2,4)]non-6-ene (20), via the reaction of 1-chloro-3-trimethylsilylcyclopropene with 1,3-cyclohexadiene. Both the tricyclic cyclopropene 15 and the anti-Bredt compound 17 were trapped by diphenylisobenzofuran (DPIBF).
authors.affiliation: Department of Chemistry, Fu Jen Catholic University, Xinzhuang , New Taipei 24205, Taiwan, R.O.C.
authors.forename: Gon-Ann
authors.initials: GA
authors.lastname: Lee
authors.forename: Hung-Chun
authors.initials: HC
authors.lastname: Lin