Abstract
Synthesis of the unknown o- m- o- m-cyclophane derivative 13 is achieved by deoxygenation of the adduct 12, derived from a bis-Diels-Alder addition of furan to the intermediate bis-aryne generated by bis-dehydrobromination of dibromide 11. The colorless photochromic cyclophanediene 13 switches to the green dibenzannulene 14 on uv irradiation, and 14 thermally or photochemically reverts to 13, with E act = 20 kcal/mole.
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