The Stereochemistry of Catalytic Hydrogenation. IV. Hexahydrodiphenic Acids

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

doi:10.1021/ja01261a004

Cited by 7 publications

(3 citation statements)

References 0 publications

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“…The former, for which structure Va appears reasonable, was readily hydrolyzed back to V; indeed treatment of Va with 2,4-dinitrophenylhydrazine precipitated the 2,4dinitrophenylhydrazone of V directly. 4 The following mechanism thus fits these facts. The intermediate dihydrochloride, CioH«C12, probably has the structure 2,4dichloro-3,6-dimethyl-3,5-octadiene.…”

supporting

confidence: 62%

The Hydration and Cyclization of some Divinylacetylenes

Hennion¹,

Davis²

1951

J. Org. Chem.

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supporting

confidence: 62%

The Hydration and Cyclization of some Divinylacetylenes

Hennion¹,

Davis²

1951

J. Org. Chem.

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“…Inaccuracies in chart calibration are less than +0.01 Hz. (32) . H. Jaffé and M. Orchin, "Theory and Applications of Ultraviolet Spectroscopy," Wiley, New York, N. Y., 1962. Isopropylidenic couplings were determined from spectra from which line broadening due to unresolved long-range couplings had been eliminated by decoupling.…”

Section: Methodsmentioning

confidence: 99%

Carbon-13 magnetic resonance. XXIV. Perhydroanthracenes and perhydrophenanthrenes

Dalling¹,

Grant²

1974

J. Am. Chem. Soc.

108

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The proton-decoupled, carbon-13 magnetic resonance (cmr) data have been determined for all of the five possible perhydroanthracene structural isomers and for four of the six possible perhydrophenanthrene compounds. The former are of known configuration, but the latter are unidentified in the chemical literature prior to the present work. The data are initially assigned to specific carbon positions using a parameter set derived from the methyldecalins. The calculated spectra are then refined by least-squares, regression analysis. New chemical shift parameters associated with boat and skew pentane conformations are discussed.he first tetradecahydroanthracene (or perhydroanthracene, abbreviated for convenience to PHA) isomer was synthesized about the turn of the century.2-4 It was soon recognized that other geometric isomers were possible6 and as many as 20 were suggested.6 Fries and Schilling ultimately delineated the correct number as being five,7 the last of which was synthesized only in recent years.8 Many workers contributed to the synthesis and characterization of the several isomers.7•9-14 X-Ray16 and electron diffraction16•17 work

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“…Hydrogenation of 79 was found more rapid in acetic acid than in ethanol; when it was stopped aer 3 moles of hydrogen had been consumed, a mixture of unreacted starting material, cis-half-hydrogenated acid 80 and perhydroacid 81 was obtained. 36 Moreover, hydrogenation of isolated 80 in the same conditions gave the same perhydrogenated acid 81 in good yield. The latter compound could be thermally converted to its trans isomer 86, whose hydrogenation gave the trans,cis,syn-perhydrogenated acid 87 in good yield.…”

Section: Substituted Biphenylsmentioning

confidence: 87%