Die Dienol??Benzol??Umlagerung von Allyldienolen: aromatische [1, 2]??,[3, 3]??und [3, 4]??sigmatropische Umlagerungen

HJ Hansen, B Sutter, H Schmid

Index: Hansen,H.-J. et al. Helvetica Chimica Acta, 1968 , vol. 51, p. 828 - 867

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Citation Number: 26

Abstract

Abstract The dienol-benzene rearrangement of syn and anti-4-allyl-4-methylcyclohexa-2, 5- dien-1-ol (syn and anti 15) occurs by formation of a benzonium ion intermediate in p-toluene- sulphonic acid in ether below 0 and leads to a mixture of 2-, 3-and 4-allyltoluenes in the ratio 54: 10: 36. By the introduction of 14 C-, D-and methyl labelled dienols it is shown that only the allyl group migrates and that this rearrangement is an intramolecular, one-step ...