Neue Umlagerungen von Aryl‐allyl‐äthern und Allylphenolen. (Vorläufige Mitteilung) | Zendy

Borgulya J. | Zendy; Hansen H.J. | Zendy; Barner R. | Zendy; Schmid H. | Zendy

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Neue Umlagerungen von Aryl‐allyl‐äthern und Allylphenolen. (Vorläufige Mitteilung)

Author(s) -

Borgulya J.,

Hansen H.J.,

Barner R.,

Schmid H.

Publication year - 1963

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19630460664

Subject(s) - chemistry , steric effects , phenols , phenol , aryl , medicinal chemistry , yield (engineering) , stereochemistry , organic chemistry , alkyl , materials science , metallurgy

In position 3 (and 5) substituted phenyl‐γ‐methyl (and phenyl)‐allylethers when subjected to the thermal C LAISEN ‐rearrangement not only yield the expected o ‐allyl‐phenols but in addition considerable amounts of the P ‐allylated phenols. Migration to the para ‐position is favoured by non‐polar solvents. This para ‐migration of the substituted allylgroup is attributed mainly to steric factors. With sterically hindered, in ortho ‐ or para ‐position allylated phenols there was furthermore found an allyl‐phenol‐rearrangement: on sufficient heating to 200° these substances are transformed to the thermodynamically more stable para ‐ resp. ortho ‐allylphenols with inversion of the allyl group.

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