Cyclopropylidene-bicyclo[1.1.0]butane interactions. The generation and intramolecular rearrangement of tetracyclo[5.1.0.02,4.03,5]octanylidenes

✍ Scribed by Leo A. Paquette; Richard T. Taylor

• Publisher: Elsevier Science
• Year: 1976
• Tongue: French
• Weight: 215 KB
• Volume: 17
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)93828-0

✦ Synopsis

Pentacyclic (CH)a hydrocarbon 1 can be viewed not only as the most highly condensed valence isomer of cyclooctatetraene, but also as a formal (2+2) dimer of tetrahedrane. The effective cyclic conjugation of two bicyclo[l.l.O]butsne rings in 1 should form the basis for interesting spectral properties." Furthermore, its highly strained nature should promote unusua,l chemical reactivity. In anticipation that double carbenoid C-H insertion of readily accessible 4,4,8,8-tetrabromotricyclo[~.1.0.03~']octanes (~2)" or *ore conventional monocyclization4 of tetracyclic dibromides such as & could provide expedient synthetic entries to 1, we have exposed. severaI such halides to methyllithium.

This approach was prompted in particular by our earlier observation that ClOSWiV Of'

proceeds in exceptionally high (91s) yield.' However as