Cope rearrangements of diels-alder adducts containing norbornene and norbornenone systems |
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Authors: | D.M. Bratby J.C. Chadwick G.I. Fray R.G. Saxton |
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Affiliation: | Department of Organic Chemistry, The University, Bristol BS8 ITS, England |
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Abstract: | The product formed from cyclopentadiene and the cyclo-octatetraene dimer 5a has been shown to possess structure 6a, probably resulting from Cope rearrangement of an initial adduct 4a. The reaction of tetraphenylcyclopentadienone with 1 - methoxybuta - 1,3 - diene yields a mixture of the exo-adduct 14 and the rearranged endo-adduct 13 Rearrangement of the norbornenone derivative 27 gives the Cope product 29 Treatment of the 4,5-fused 2,3,4,5-tetrachlorocyclopent-2-enones 29,40 and 41 with powdered sodium hydroxide in tetrahydrofuran results in ring-cleaveage with the formation of 2,3,5-trichlorobuta-2,4-dienoic acid derivatives, 36, 43 and 44 respectively. |
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