Synthese des Iso‐axerophtens

Karrer, P.; Karanth, K. P.; Benz, J.

doi:10.1002/hlca.19490320212

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E Anomalous Reactions1

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2011

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Cited by 10 publications

(1 citation statement)

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“…6j3,16a-Dihydroxy-3,5-cyclo-androstan-17-one under the acid conditions of a Girard-T separation was converted into 16 a-hydroxydehydroepiandrosterone through loss of the 6/3-hydroxy group and opening of the cyclopropane ring (61). The acid sensitive ketone XXXVIII, 8-(2,6,6-trimethyIcyclohex-2-enyl)-octa-3,-OH 5,7-triene-2-one is rearranged to the fully conjugate ketone, but forms an unrearranged hydrazone with Girard-P reagent in the absence of acetic acid (96).…”

Section: E Anomalous Reactionsmentioning

confidence: 99%

The Girard Reagents.

Wheeler¹

1962

Chem. Rev.

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Section: E Anomalous Reactionsmentioning

confidence: 99%

The Girard Reagents.

Wheeler¹

1962

Chem. Rev.

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The Oppenauer Oxidation

Djerassi¹

2011

Organic Reactions

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The application of the reduction of aldehdyes and ketones has been reviewed in an earlier chapter (The Meerwin‐Pondorff‐Verley reduction). The reversible nature of the reaction was demonstrated by Verley, but it was not until 1937 that Oppenauer showed that unsaturated steroid alcohols could be oxidized to the corresoponding ketones in excellent yield using aluminum t‐butoxide. In the presence of a large amount of acetones. Acetone functions as the hydrogen acceptor and the large excess serves to shift the equilibrium into the desired direction. This reaction is called the Oppenauer reaction hand is useful in steroid chemistry. The Oppenauer oxidation employs mild conditions so it will undoubtedly find use in synthetic organic chemistry. The recent experimental modifications are discussed here.

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Reductions by Lithium Aluminum Hydride

Brown

2011

Organic Reactions

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Lithium aluminum hydride is a useful and convenient reagent for the selective reduction of various polar functional groups. It is used in diethyl ether solution, less commonly in higher boiling ethers, following the conventional procedures for syntheses employing the Grignard reagents, which the hydride closely resembles in its general pattern of behavior. The reaction proceeds with extraordinary rapidity and is relatively free of side reactions. The types of organic compounds reduced by lithium aluminum hydride and the nature of the products are detailed in this chapter. Functional groups not reduced are discussed.

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Synthese des Iso‐axerophtens

Abstract: Auf ähnlichem Wege, auf dem früher der Kohlenwasserstoff Axerophten synthetisiert worden war, wurde – ausgehend vom α‐Jonon – das Iso‐axerophten dargestellt, welches an Stelle eines β‐einen α‐Jononkohlenstoffring enthält.

Cited by 10 publications

References 10 publications

The Girard Reagents.

The Girard Reagents.

The Oppenauer Oxidation

Reductions by Lithium Aluminum Hydride

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