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 | Zendy

König Burkhard | Zendy; Meijere Armin De | Zendy

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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

Author(s) -

König Burkhard,

Meijere Armin De

Publication year - 1992

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19921250817

Subject(s) - chemistry , phenylmagnesium bromide , yield (engineering) , medicinal chemistry , bromide , diels–alder reaction , reactivity (psychology) , naphthalene , diene , benzoquinone , organic chemistry , polymer chemistry , catalysis , medicine , materials science , alternative medicine , pathology , reagent , metallurgy , natural rubber

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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