Carbon-carbon bond fission in cyclopropanes III. The acid promoted opening of the three-membered ring in exo-tricyclo[3.2.1.02,4] octane

✍ Scribed by Robert T. LaLonde; Joseph J. Batelka

• Publisher: Elsevier Science
• Year: 1964
• Tongue: French
• Weight: 250 KB
• Volume: 5
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)90358-7

✦ Synopsis

In our search for appropriate substrates which might be employed in a study of the mode of electrophilic attack of strained carbon-carbon bonds, we have iuvestigated the acid promoted cleavage of the three-membered ring in em-tricyclo~.2.1.02~~octaue, I. I In this cmmuuication we report and discuss our preliainary results. The treatment of I with glacial acetic acid, 0.07N in sulfuric acid, for fifty hours at rocm temperature produced a mixture of olefins (20%) aud acetates (SC$). The acetate ccmponent MS shown by gas chmuatographic analysis (Carbowax at 159") to consist of five poorly resolved acetates. The acetates uere converted by lithium alumiuium hydride hydrogenolysis to a mixture of alcohols whose gas chromatogram, obtained by eaploying a 17$ glycerol on Celite column at 103', demonstrated the preseme of ~L?L? alm!mIK The predomiuant alcohol MS pressnt in 44% of the alcohol fraction and its gas chromatographic retention time (peak 4, 45 min.) wa8 ideutical with that of u-2-bicyclo~.2.~octauol, II (R=H). The next moat abundant *Paper II in this 8eries: &. % 3771 (1963).