Wagner-Meerwien rearrangement of allylbenzene derivatives. I. Bromination of safrole.

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 1975 English Publisher:Pharmaceutical Society of JapanJournal:Chemical and Pharmaceutical Bulletin, volume 23, pages 646-650 (issn: 0009-2363, eissn: 1347-5223,

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Authors: TAEKO IRINO; KAZUO OTSUKI;

doi: 10.1248/cpb.23.646

Wagner-Meerwien rearrangement of allylbenzene derivatives. I. Bromination of safrole.

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Abstract

The reaction of safrole (I) with bromine (II) was examined giving different results from the literature, i.e., 2, 3-dibromo-1-(3', 4'-methylenedioxyphenyl) propane (III), 1, 3-dibromo-2-(3', 4'-methylenedioxyphenyl) propane (V) and their bromo-substituted derivatives (IV and VI) were obtained. The formation of rearranged adducts (V and VI) suggests that Wagner-Meerwein rearrangement occured during this addition. The relationship between the reaction conditions and the ratio of the products was investigated.

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