Isolation and valency isomerization of cis-cis-cis-1,3,5-cyclononatriene

✍ Scribed by David S. Glass; J.W.H. Watthey; S. Winstein

• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 274 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89963-3

✦ Synopsis

It was reported recently (3) from this Laboratory that cis-cis-cis-1,4,7-cyclononatriene I is isomerized by potassium t-butoxide (KOBu) in dimethylsulfoxide (DMSO) to the cis-cis-cis-1,3,6:isomer 11 and then to the bicyclic isomer, (4) cis-bicyclo[4. 3.O]nona-P, rl-diene IV. Although cis-cis-cis-1,3, S-cyclononatriene III was not observed, it was suspected to be an intermediate for the formation of IV by valency tautomerism. Since the III -IV valency isomerization is of considerable interest, we sought to detect and actually isolate III. This has proved to be possible, and we have now been able to study directly-the III-IV transformation.