Contractive Annulation: A Strategy for the Synthesis of Small, Strained Cyclophanes and Its Application in the Synthesis of [2](6, 1)Naphthaleno[1]paracyclophane. Issue 27 (27th May 2019)

• Record Type: Journal Article
• Authors: Biswas, Sourav; Qiu, Christopher S.; Dawe, Louise N.; Zhao, Yuming; Bodwell, Graham J.
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 27(2019)
• Page Start: 9166
• Page End: 9170
• Publication Date: 2019-05-27
• Subjects: aromaticity -- annulations -- cyclophanes -- strained molecules -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201904673
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A new synthetic strategy (contractive annulation) for the synthesis of highly strained cyclophanes has been conceived and its viability has been demonstrated through a nine‐step synthesis of [2](6, 1)naphthaleno[1]paracyclophane from [2.2]paracyclophane. Abstract : Autocannibalism? One of the bridge atoms of [2.2]paracyclophane has been used as food for the growth of one of the aromatic units from benzene to naphthalene. In so doing, a new way of generating small, strained cyclophanes has been realized, as shown for the nine‐step synthesis of [2](6, 1)naphthaleno[1]paracyclophane from [2.2]paracyclophane.