Stereoselectivity in the thermal rearrangement of 3,4-bistrimethylsiloxy-1,5-hexadiynes.

✍ Scribed by N. Manisse; J. Chuche

• Book ID: 104214992
• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 204 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75084-2

✦ Synopsis

The thermal rearrangement of a number of substitued 1,5-hexadiynes has been reported 1 to lead to bismethylene cyclobtraene derivatives . Qr the other hand, pyrocatechol 2 and 3,5-octadiene-2,7-dione 3 respectively, were obtained in poor yields when 1,5-hexadiyne-3,4diol s and 3,4-dimethyl-1,5-hexadiyne-3,4-dial 2 were pyrolysed. In or&r to minimize the formaticol of polymers and fragmentation prklucts 4, and to facilitate the study of the mechanism of these last reactions, we have prepared and submitted to thermolysis the compound 2

ScZHEME I (UTms -0-Si(CH3)3)