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Stereochemie von α,ω-Diphenyl-alkan-α,ω-diolen

Stereochemistry of α,ω-diphenylalkane-α,ω-diols; Cyclization and determination of the diastereomeric ratio of the diols formed upon reduction of α,ω-diphenylalkane-α,ω-diones

Cyclisierung und Bestimmung des Diastereomerenverhältnisses der bei der Reduktion von α,ω-Diphenyl-alkan-α,ω-dionen gebildeten Diole

  • Organische Chemie und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Reduction (both catalytically and with complex hydrides) of the diphenyl diketones1 (a, b, c andd withn=0, 2, 3 and 4) was investigated mainly with regard to the diastereomeric ratio of the diols2. For2 a and2 b exact results were obtained by NMR spectroscopy (without or with shift reagents) of the diol mixture (2 a) or after stereoselective cyclization to the cyclic ethers (3 b). AlsoGC andLLC were employed for the analysis of2 a (GC of the trimethylsilyl derivatives) and for the ethers3, resp. (GC for3 a and3 d;LLC for3 b and3 c).

The reduction of1 a, 1 b (and in part1 c) proceeds with high stereoselectivity; themeso-diol preponderates in the case of2 a, therac.-diol for2 b and2 c; with increasingn the diastereomeric ratio approaches the statistical ratio of 1∶1.

Preparations of the stereoisomeric diols (2 b, c andd via acetylenic precursors) and of the cyclic diphenyl ethers (by stereoselective cyclization and/or chromatographic separation;3 c and3 d for the first time) as well as the determination of their configurations are described. The latter was achieved by NMR and for the ethers3 also by hydrogenation of the corresponding heteroaromatics.

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  1. Lehrkanzel für Organische Chemie, Universität Wien, Währinger Straße 38, A-1090, Wien, Österreich

    Horst Neudeck & Karl Schlögl

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  1. Horst Neudeck
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Neudeck, H., Schlögl, K. Stereochemie von α,ω-Diphenyl-alkan-α,ω-diolen. Monatshefte für Chemie 106, 229–259 (1975). https://doi.org/10.1007/BF00914517

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