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A bridged triptycene-intramolecular diels-alder reaction of 16,19-dimethoxy-[2](9,10)anthraceno[2]paracyclophane

✍ Scribed by Yoshimasa Fukazawa; Masato Kikuchi; Osamu Kajita; Shô Itô

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 266 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80198-2

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✦ Synopsis

A bridged triptycene was obtained by intramolecular cycloaddition reaction of 16,19-dimethoxy[ZJ (9,lO)anthracenomparacycIophane followed by acid-cotoiyzed elimination of methanol. Internal strain in this molecule was disclosed by X-ray crystallographic analysis. Lice and C. G.

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## Abstract The title compounds 8 and 1 have been synthesized in three steps each from 1,2‐dibromo[2.2]paracyclophan‐1‐ene (2) and 1,2,9,10‐tetrabromo[2.2]paracyclophane‐1,9‐diene (4), respectively. Copper‐mediated coupling of vinyl bromides 2 and 4 with methyl‐ and phenylmagnesium bromide gives su