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The ortho-quinol acetates (die ortho-Chinolacetate): 20 years of dedicated research in Vienna and what happened then?

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Abstract

o-Quinol acetates (o-Chinolacetate) were the main research field of the Organic Chemistry Institute in Vienna (Austria) for two decades beginning in 1950. The possibility to react them with various kinds of compounds was exploited for the synthesis of structural types not easily accessible on other ways. They became the basis for investigations, e.g. in photochemistry, in reaction mechanistic studies of various rearrangement reactions, or the Diels–Alder reaction. Even in the natural products chemistry o-quinol structures can be found comprising Diels–Alder dimeric terpenes. Most of the original publications had appeared in Monatshefte für Chemie written in German. This might explain a statement from the year 2000 that “These findings add to our knowledge of the largely unexplored chemistry of o-quinols….” (Nicolaou et al. in J Am Chem Soc 122:3071, 2000). This review is intended to wake up slumbering knowledge.

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Notes

  1. Prof. Dr. Friedrich Wessely von Karnegg was born 1897 in Kirchberg (Niederösterreich), gravely wounded in the first WW. He studied chemistry at the University in Vienna (Austria) and was head of II. Chemisches Institut there from 1948 until his death in 1967.

  2. The German term “Chinol” indicates a hydroxy cyclohexadienone structure. The English term "quinol" is ambiguous, it can also mean benzene-1,4-diol (hydroquinone). In this review it will not be used in that meaning.

  3. Occasionally a different numbering system is used, viz. 6-acetoxycylohexa-2,4-dienone. The IUPAC name of 1b is 1-methyl-6-oxocyclohexa-2,4-dien-1-yl acetate.

  4. The last contributions to Monatshefte für Chemie where most of the research results from Vienna had been published, appeared in 1968 [4, 5].

  5. Surveys of the o-quinol acetate chemistry I am aware of stem from the early days [8, 9] or cover only parts of the field [6].

  6. Wessely's [17] interest in such compounds is also documented by the PbTA oxidation of p-HO-C6H4–CH(C2H5)–CH(C2H5)–C6H4-p-OH yielding a bis-o-quinone diacetate.

  7. To avoid repeated quotation of the lengthy name of the 101a dimer, (1S,2S,3R,7R,8S,10R)-3,10-dihydroxy-6,12-diisopropyl-3,10-dimethyltricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione (101c), Van Dongen introduced the name “dielmenthane” for the hydrocarbon skeleton of the 101a dimer (101d). 101c is named 3,10-dihydroxy-dielmentha-5,11-diene-4,9-dione [193]. This shorthand version has been used in several publications not only by the author.

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  1. Institut für Organische Chemie, Universität zu Köln, Greinstr. 4, 50939, Kölm, Germany

    Herbert Budzikiewicz

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Budzikiewicz, H. The ortho-quinol acetates (die ortho-Chinolacetate): 20 years of dedicated research in Vienna and what happened then?. Monatsh Chem 147, 627–663 (2016). https://doi.org/10.1007/s00706-015-1635-0

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