Systematic classification and nomenclature of diamond hydrocarbons—I: Graph-theoretical enumeration of polymantanes

Evaluation of the effect of strain upon reactivity

Synthesis of 1,3-Disubstituted Adamantanes.



A series of new 1-substituted 3-bromoadamantanes has been prepared. An improved method for the formation of cyclopropanes from olefins with diazomethane and copper salts is described.

Die Synthese von 1,3‐disubstituierten Adamantanen

Aryl-, Alkyl-, Cycloalkyl-, Polycycloalkyl- und Benzyl-Radikale wurden aus Persaureestern 1 oder (Arylazo)triphenylmethan durch Thermolyse in CCl4/BrCCl3 erzeugt; ihre Selektivitat bei der konkurrierenden Halogenubertragung von BrCCl3 und CCl4 wurde durch gaschromatographische Produktanalyse bestimmt Die Konkurrenzkonstanten r sinken in der Reihe Benzyl- > Alkyl- > Aryl- > Bruckenkopf-Radikal, wofur das Selektivitatsprinzip10) verantwortlich gemacht wird Sterische und polare Effekte beeinflussen die Konkurrenzkonstanten ebenfalls deutlich Es besteht keine einfache Beziehung zwischen der Bildungsgeschwindigkeit der Radikale aus den Perestern und ihrer Selektivitat – Der Anteil an Kafigrekombination bei der Thermolyse von Cycloalkanpercarbonsaureestern mit 5 – 12 Ringgliedern sinkt parallel mit zunehmender Masse der beteiligten Radikale



Organic Peroxides, XIX Relation between Stability and selectivity of Carbon Radicals



Aryl, alkyl, cycloalkyl, polycycloalkyl, and benzyl radicals were generated by thermolysis of peresters 1 or (arylazo)triphenylmethanes in CCl4/BrCCl3 The selectivity of the competing halogen transfer from BrCCl3 and CCl4 was determined by gaschromatography of the products The selectivity relationship10) is made responsible for the decreasing of the competition constants r in the series benzyl > alkyl > aryl > bridgehead radicals In addition steric and polar effects determine the size of the competition constants No relationship is recognized between the rate of radical production from peresters 1 and their selectivity – The yields of cage recombination product in the thermolysis of tert-butyl cycloalkanepercarboxylates (n = 5 – 12) in CCl4 decrease regularly with increasing mass of the cycloalkyl radicals

Organische Peroxide, XIX. Zur Frage der Stabilität und Reaktivität von Kohlenstoffradikalen

Conformational effects in compounds with 6-membered rings—XIII : Detection of twist conformers using 13C NMR chemical shifts

[2]Diadamantane, the first member of a new class of diamondoid hydrocarbons

Homoadamantan-1-ol (14) wurde ausgehend von 5-Hydroxy-2-adamantanon (13) durch Ringerweiterung mit Diazomethan und Entfernung der Carbonylgruppe auf eindeutige Weise dargestellt. Die Struktur der Homoadamantan-1- carbonsaure (5), die aus 1 unter Koch-Haaf-Bedingungen nach langer Reaktionszeit erhalten wurde, konnte durch Abbau zum gleichen Alkohol 14 bestatigt werden. 13C-NMR-Spektren unterstutzen die Struktur zuordnung der 1- und 3-Homoadamantane. Das 3-Homoadamantyl-Kation (16) ist stabiler als das 1-Kation 17, aber Substitutenten sind in der 1-Position wegen differentieller sterischer Effekte der benachbarten Methylengruppen stabiler als in der 3-Position. Dies wird durch Computerrechnungen verschiedener Konformationen bestatigt.



Bridgehead Homoadamantane Derivatives. Structural Evidence



Homoadamantan-1-ol (14) was synthesized unambiguously from 5-hydroxy-2-adamantanone (13) by diazomethane ring enlargement followed by removal of the carbonyl group. The structure of homoadamantane-1-carboxylic acid (5), obtained from 1 under Koch-Haaf conditions and long reaction times, was confirmed by degradation to the same alcohol, 14. 13C.n.m.r. spectra provide further support for 1- and 3-homoadamantane structural assignments. The 3-homoadamantyl cation (16) is more stable than the 1-cation 17, but substituents are more stable at the 1- rather than at the 3-position due to differential steric effects of the adjacent methylene groups. Computer conformational analysis calculations confirm this conclusion.

Zur Struktur von Brückenkopfderivaten des Homoadamantans

Stable carbocations. Part 235. Solvolytic and stable ion studies of 1,1'-diadamantylmethyl cations

Struktur von brueckenkopfderivaten des homoadamantans

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[2]Diadamantane, the first member of a new class of diamondoid hydrocarbons

Zur Struktur von Brückenkopfderivaten des Homoadamantans

Stable carbocations. Part 235. Solvolytic and stable ion studies of 1,1'-diadamantylmethyl cations

Struktur von brueckenkopfderivaten des homoadamantans