Multiple aromatische sigmatropische Umlagerung von γ, γ‐Dimethylallyl‐phenyläther

Helvetica Chimica Acta - Tập 51 Số 7 - Trang 1603-1608 - 1968
Feodor Scheinmann1, Richard Barner1,2, H. Schmid1
1Organisch-chemisches Institut der Universität Zürich
2Physikalisch-chemische Abteilung der Fa. HOFFMANN-LA ROCHE & CO. AG., Basel.

Tóm tắt

Abstract

The rearrangement of γ,γ‐dimethylallyl phenyl ether (1), contrary to previous reports, gives a mixture of 4‐(γ,γ‐dimethylallyl)‐phenol (2), 2‐(α,β‐dimethylallyl)‐phenol (3) and 2,2,3‐trimethylcoumaran (4). The ratio of the reaction products is dependent on the solvent and the reaction temperature. The mechanism for the reaction is discussed in terms of multiple sigmatropic rearrangements.

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Tài liệu tham khảo

10.1002/prac.19221050107

10.1002/cber.19260590927

10.1002/cber.19250580207

10.1021/ja01526a021

10.1002/hlca.19630460664

Gy.Fráter Dissertation Universität Zürich1967.

Jefferson A., Chem. Commun., 1966, 239

Jefferson A., Quart. Rev., 1968

H.Schmid Vortrag am Symposion der Chemical Society über Stereochemie Sheffield Dez.1966.

10.1021/ja01299a024

10.1021/jo01070a001

10.1021/jo01045a528

10.1002/hlca.19620450628

10.1002/hlca.19650480611

10.1021/jo01059a068

10.1021/ja00982a023

10.1021/ja01242a043

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Helvetica Chimica Acta

Tập 51 Số 7

1603-1608

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