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- W1999531520 abstract "trans-Penta-2, 4-dienyl phenyl ether (trans-1), on heating at 186° in a five-fold excess of N, N-diethylaniline, gave via a [3s, 3s] rearrangement 23% of 2-(1-vinyl-allyl)-phenol (2) and via a [5s, 5s] rearrangement 37% of trans-4-(penta-2, 4-dienyl)-phenol (trans-3). The dimeric residue was formed from trans-1 by diene synthesis. By working at high dilution, the formation of dimeric products was kept to a minimum. The inversion of the migrating pentadienyl residue during the rearrangement of trans-1 to trans-3 was proved by rearrangement of the methyl labelled ether trans, trans-4 to the p-dienyl-phenol 8 (93%) (accompanied by only 7% of 9). trans-5 gave the p-phenol 9 quantitatively. cis-Penta-2, 4-dienyl phenyl ether (cis-1) was converted to 10 on heating, by a fast [1, 5s] H-migration. The above mentioned reactions of the type trans-1 → trans-3 show first order kinetics and are the first examples of [5s, 5s] sigmatropic rearrangements shown to go through a ten-membered transition state. The conformation of the activated complex is discussed in the light of the stereochemistry of the migrating penta-2, 4-dienyl group." @default.
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- W1999531520 date "1970-01-01" @default.
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- W1999531520 title "Thermische Umwandlung von Penta-2, 4-dienyl-phenyläthern in 4-(Penta-2, 4-dienyl)-phenole; [5s, 5s]-sigmatropische Umlagerungen" @default.
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- W1999531520 doi "https://doi.org/10.1002/hlca.19700530208" @default.
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