Synthesis of 2,3-Dibromobenzonorbornadiene and its Cyclotrimerization into 5,18:6,11:12,17-Trimethanotrinaphthylene

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• 作者：Cossu ; Sergio ; De Lucchi ; Ottorino ; Lucchini ; Vittorio ; Valle ; Giovanni ; Balci ; Metin ; Dastan ; Arif ; et. al.
• 刊名：Tetrahedron Letters
• 出版年：1997
• 出版时间：July 28, 1997
• 年：1997
• 卷：38
• 期：30
• 页码：5319-5322
• 全文大小：253 K

文摘

The synthesis of 2,3-dibromobenzonorbornadiene 11 by high temperature bromination of 2-bromobenzonorbornadiene 9 allows the synthesis of the benzoannelated trimers, syn- and anti- 5,18:6,11:12,17-trimethanotrinaphthylene 8. The syn isomer is a basket shaped molecule that displays unusual geometric and electronic features including bond length fixation of the central benzene ring as shown by X-ray diffraction (exocyclic bond 1.41 Å, endocyclic bond 1.36 Å).