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Synthesis and Diels-Alder Reactions of 1,2-Dimethylene- and 1,2,9,10-Tetramethylene[2.2]paracyclophane: New Routes to Bridge-Anellated [2.2]Paracyclophanedienes

✍ Scribed by König, Burkhard ;Meijere, Armin De

Publisher
Wiley (John Wiley & Sons)
Year
1992
Tongue
English
Weight
472 KB
Volume
125
Category
Article
ISSN
0009-2940

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✦ Synopsis

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 substituted [2.2]paracyclophanes 3‐CH~3~, 3‐Ph, 5‐CH~3~, and 5‐Ph in good yields. The high reactivity of the [2.2]paracyclophane‐1,2‐dimethylene moieties in 8 and 1 in Diels‐Alder reactions has been verified in cycloadditions with p‐benzoquinone to give 10 and 13 and with naphthalene 1,4‐endoxide to yield 12.

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