The Stereochemistry of Catalytic Hydrogenation. V. The Assignment of cis- and trans-Configurations

Linstead, R. P.; Davis, Selby B.; Whetstone, R. R.

doi:10.1021/ja01261a005

Cited by 6 publications

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“…1) is of critical importance for the interpretation of the experiments to be reported. Tritiation of the A 1 bond of A 1 ^-steroids with palladium on charcoal yields 75-90% tritiation in the l a and 2a positions, due to catalytic attack at the aside of the steroid molecule (8)(9)(10). The stability of this type of 1,2-tritium labeling has been studied intensively by Osinski (11), who demonstrated that drastic chemical treatment (1 M KOH in 75% aqueous methanol at elevated temperatures, chromic acid oxidation, reduction with lithium aluminum hydride, acetylation with acetic anhydride in pyridine) did not alter the specific This work was supported by Grants A-3270 and A-3269, National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, Public Health Service, USPHS.…”

Section: Mechanism Of Biochemical Aromatization Of Steroidsmentioning

confidence: 99%

Mechanism of Biochemical Aromatization of Steroids

Axelrod

Goldzieher

1962

The Journal of Clinical Endocrinology & Metabolism

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Section: Mechanism Of Biochemical Aromatization Of Steroidsmentioning

confidence: 99%

Mechanism of Biochemical Aromatization of Steroids

Axelrod

Goldzieher

1962

The Journal of Clinical Endocrinology & Metabolism

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Zur Photochemie von 1,5‐Cyclodecadienen und 1,2‐Divinylcyclohexanen

Gotthardt

Hammond

1976

Chem. Ber.

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Die benzol-sensibilisiere Bestrahlung (2537 A) von cis,trans-1,5-Cyclodecadien (1) liefert eine Produktmischung aus 1, trans-1,2-Divinylcyclohexan (2), cis-1,2-Divinylcyclohexan (3) und cis,cis-1,5-Cyclodecadien (4) sowie eine gesattigte Verbindung der Konstitution cis-5 als Ergebnis einer intramolekularen, gekreuzten Cycloaddition. Die gleichen Produkte, allerdings in anderen Verhaltnissen, werden auch bei der Belichtung von 4 erzielt. Interessanterweise wird 3 bei der benzol-sensibilisierten Photoreaktion in cis-5 iibergefiihrt; 2 ergibt dagegen 3, Spuren cis-5 und eine Verbindung unbekannter Konstitution. On the Photochemistry of 1,s-Cyclodecadienes and 1,2-DivinylcyclohexanesBenzene sensitized irradiation (2537 A) of cis,rrons-1,5-cyclodecadiene (1) yields a mixture of products consisting of 1, trans-1,2-divinylcyclohexane (2), cis-1,2-divinylcyclohexane (3), and cis,cis-1,5-cyclodecadiene (4) together with a saturated compound of structure cis-5 as a result of a crossed cycloaddition. The same products but in other product ratios are obtained from irradiation of 4. Interestingly, the benzene sensitized photochemical reaction of 3 affords cis-5; 2 yield 3, traces of cis-5, and a compound of unknown structure.Unter den zahlreichen beschriebenen Photoreaktionen von Olefinen, die zwei oder mehrere formal isolierte Doppelbindungen 3 -' ) enthalten, findet man nur wenige Studien iiber Verbindungen dieses Typs im Bereich der mittleren Ringe. So beobachtete man in mittleren und groDeren Ringen cisltrans-Isomerisierungen ' ~ und Positionswechsel 1 3 ) I ) Versuche 1965/66, ausgefiihrt in den Gates and Crellin Laboratories of Chemistry, Cali-

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Fused Ring Systems

Talapatra

Talapatra²

2022

Basic Concepts in Organic Stereochemistry

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The Stereochemistry of Catalytic Hydrogenation. V. The Assignment of cis- and trans-Configurations

Cited by 6 publications

References 0 publications

Mechanism of Biochemical Aromatization of Steroids

Mechanism of Biochemical Aromatization of Steroids

Zur Photochemie von 1,5‐Cyclodecadienen und 1,2‐Divinylcyclohexanen

Fused Ring Systems

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