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2 article(s) from Schäfer, Hans J

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

Matthias C. Letzel,
Hans J. Schäfer and
Roland Fröhlich

Beilstein J. Org. Chem. 2017, 13, 33–42, doi:10.3762/bjoc.13.5

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Figure 1: Menthol auxiliaries 1–4 used in the following anodic coupling reactions.

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Scheme 1: Synthesis of carboxylic acids 13a/b–18a/b.

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Scheme 2: (a) Preparation of benzyl 2-isopropylmalonate (5) and (b) preparation of benzyl 2-tert-butylmalonat...

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Scheme 3: Coelectrolysis (hetero-coupling) of carboxylic acids 13–17 with 3,3-dimethylbutyric acid (20).

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Figure 2: Crystal structure of the minor diastereomer 23b.

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Figure 3: Cyclic voltammograms of the malonic derivatives 15a/b, 16a/b and 18a/b (scan rate: 500 mA/s, solven...

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Scheme 4: Homo-coupling of carboxylic acids 13a/b–16a/b to diesters 26a/b/c–29a/b/c (n.d.: not determined).

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Figure 4: Crystal structure of major diastereomer 28a.

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Figure 5: Crystal structure of major diastereomer 29a.

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Figure 6: Discrimination of diastereomeric faces in the menthol substituted radical A and in the 8-phenylment...

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Scheme 5: Reductive cleavage of 30a–c to 8-phenylmenthol (3) and 31a–c.

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Published 05 Jan 2017

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Cathodic hydrodimerization of nitroolefins

Michael Weßling and
Hans J. Schäfer

Beilstein J. Org. Chem. 2015, 11, 1163–1174, doi:10.3762/bjoc.11.131

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Scheme 1: Proposed mechanisms via pathways (I) to (III) for the cathodic hydrodimerization of olefins with el...

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Scheme 2: Cathodic reduction of nitroalkene 1 to hydrodimer 2 and oxime 5.

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Scheme 3: Preparation of the 1-aryl-2-nitroalkenes 1, 4, 8–15.

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Scheme 4: Reduction potentials (E_p,c in Volt) of nitroolefins. Conditions: amalgamated gold wire, v = 0.1 V/s...

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Figure 1: (a) CV of 15; v = 0.1 V/s, (b) CV of 15; v = 10 V/s.

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Scheme 5: Hydrodimerization of nitroalkene 14 and 15.

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Scheme 6: (a) Intramolecular hydrocoupling of dinitrodiene 16 and (b) hydrodimerization of 1-nitrocyclohexene...

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Scheme 7: Possible stereoisomers and their mirror images for the hydrodimers 2 and 18–23; R and S are the con...

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Figure 2: ¹H NMR spectrum of 18b (without aromatic H); below experimental spectrum, above: simulated signals ...

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Published 14 Jul 2015

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