9,10-dimethylenetricyclo[5.3.0.02,8]deca-3,5-diene

✍ Scribed by Leo A. Paquette; Jürgen Dressel; Paul D. Pansegrau

• Book ID: 104227965
• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 196 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96671-1

✦ Synopsis

The title compound (3), a molecule whose central cyclobutane ring is 1,3-bonded in hybrid fashion to two butadiene units, has been prepared and its thermal stability assessed relative to 1 and 2. The recently completed syntheses of l* and 23 has permitted detailed analysis of the extent to which their central cyclobutane bonds can interact with mutually perpendicular ?r systems of different size. 4 Whereas 1 is intrinsically more capable of efficient relay conjugation than is spiro[4.4]nonatriene of through-space spiroconjugation, 5 2 differs significantly. Only a minute (< 0.1%) 2a2(z)-3a2(s*) interaction is seen by photoelectron spectroscopy.6 4 5