Synthesis of a “Molecular Pinwheel”: [3.3.3.3.3.3](1,2,3,4,5,6)Cyclophane

✍ Scribed by Youichi Sakamoto; Naomi Miyoshi; Prof. Dr. Teruo Shinmyozu

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 268 KB
• Volume: 35
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.199605491

✦ Synopsis

Cyclophane 1, a compound we have long sought""' and one of the final target molecules in the field of [3,3]cyclophane chemistry, has finally been synthesized and characterized. We expect 1 to have fascinating chemical and structural features. A photochemical isomerization of 1 to the propella[3,]prtsmane 2 (Scheme 1) has been predicted based on 1 2 Scheme 1 . Predicted photochemical isomerization of 1 to the prope!la[3,]prismane 2. semiempirical MO calculation^,^^^ and a correlated inversion of the six trimethylene chains, which resemble six blades of a pinwheel, is expected in solution (Scheme 2).[41 l a l b Scheme 2 Predicted most stable conformations and correlated inversion of the six trimethylene bridges of 1 [