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

Helvetica Chimica Acta - Tập 46 Số 6 - Trang 2444-2445 - 1963
J. Borgulya1, H.‐J. Hansen1, Richard Barner1, H. Schmid1
1Organisch-Chemisches Institut der UniversitÄt Zürich

Tóm tắt

Abstract

In position 3 (and 5) substituted phenyl‐γ‐methyl (and phenyl)‐allylethers when subjected to the thermal CLAISEN‐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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Tài liệu tham khảo

D. S.Tarbell Organic Reactions II 1 (1944).

10.1021/jo01059a068

10.1002/hlca.19620450628