Stereochemistry of a thermal rearrangement in the (CH)12 series. Establishment of the suprafacial nature of a [1,5] carbon migration

✍ Scribed by Leo A. Paquette; John C. Stowell

• Book ID: 104239968
• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 248 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88642-1

✦ Synopsis

Heating of cis,syn,cis-tiicyclo~8.2.0.02~s ]dodeca-5,5,7,ll-tetraene (9 at 120' for 24 hr has been reported to result in the formation of equal smouuts of benzene end hydrocarbcm 2. i lhe stereochemistry of cwas not determined. l?xethermlrearraugemsnt of&to 2 form&y involves the [lj5] migration of C-l frau C-2 to C-6, a sigmatropic change which, In contrast, irradiation of 6_unaer triplet conditions (acetone solution