Highly strained but thermally stable: Tetrabenzocyclophane 1, which was obtained in a four-step synthesis by two Diels - Alder addition reactions (see scheme) sublimes at high temperature, rather than decomposing. The distorted aromatic rings are more reactive with tetracyanoethylene than those in [2.2]paracyclophane. Another consequence of heightened strain is a bathochromic shift of the cyclophane band to 330 nm, the longest wavelength absorption for this band to date.
|Number of pages||4|
|Journal||Angewandte Chemie - International Edition|
|Publication status||Published - Oct 4 2002|
- Density functional calculations
- Strained molecules
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