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Open Access The von Auwers Reaction – History and Synthetic Applications

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Dienones obtained from the facile dearomatization of phenols, can be further transformed to semi-benzenes prone to rearomatize in clean, but sometimes unexpected, fashion. Over a hundred years ago, K. von Auwers found that adding Grignards on dienones would lead spontaneously to subsequent dehydration and a novel aromatizing rearrangement. This reaction was ignored for 50 years before Melvin Newman re-investigated these findings, studied the mechanism, and developed variations on the same theme. Since then, despite the tremendous potential of the reactions, those studies were only rarely mentioned, before finally falling into oblivion. This review aims to provide the reader with a detailed history and comprehensive bibliography of the von Auwers rearrangement, some of its synthetic applications, and new unpublished material in the hope to open new perspectives on this forgotten reaction.

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Keywords: RADICAL; REAROMATIZATION; REARRANGEMENT; SEMI-BENZENE; VON AUWERS REACTION

Document Type: Research Article

Affiliations: 1: Syngenta Crop Protection Münchwilen AG, Schaffhauserstrasse CH-4332 Stein, Switzerland. [email protected] 2: Syngenta Crop Protection Münchwilen AG, Schaffhauserstrasse CH-4332 Stein, Switzerland

Publication date: August 1, 2014

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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