Synthesis of [2.0.2.0]metacyclophanediene and bi-4,5-phenanthrylene

✍ Scribed by Bengt Thulin; Olof Wennerström

• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 125 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92794-7

✦ Synopsis

Non-planar aromatic molecules are now well-known. Many examples can be found among the cyclophanes 1 and helicenes, 2 and the circulenes 3 are especially interesting.

[n]Circulenes with na 7 have too long a periphery and too short an inner ring and should be saddle-shaped.

So far 0~7 hetero 171 and [8lcirculenes are known.3'4 They are all planar or nearly planar.

A "hexa J circulene" with two hydrogens instead of one unsaturated bridge, 2, has recently been reported. 5

In this paper we report the facile synthesis of bi-4,5_phenanthrylene, _2,(Scheme 1) a non-planar ~.0.2.0]met~~clophanediene, 1, and analogue of 8 circulene lacking two unsaturated bridges.