Scientific article

Die Isomerisierung der Homoadamantan-3-carbonsäure zur Homoadamantan-1-carbonsäure

Other titleThe lsomerisation or Homoadamantane-3-carboxylic Acid into Homoadamantane-1-carboxylic Acid
Published inChemische Berichte, vol. 115, p. 1509-1524
Publication date1982

lt is shown by D-, 13C-, and double labelling experiments that the title isomerisacion 2 → 3 unter Koch-Haaf conditions is due to reversible decarbonylation followed by intermolccular hydride transfer between the bridgehead positions of the two bridgehead homoadamantane cations and homoadamantane derivatives. The isomerisation is accompanied by complete equilibration of an isotopically labelled methylene group over all possible positions. This is due to the known adamantylmethyl-3-homoadamantyl cation rearrangement which is likewise occuring. In contrast to hydride transfer reactions in the adamantyl system the methylene groups of the homoadamantyl system are not participating in the hydride transfer between the bridgehead positions.

Citation (ISO format)
LANGHALS, Heinz et al. Die Isomerisierung der Homoadamantan-3-carbonsäure zur Homoadamantan-1-carbonsäure. In: Chemische Berichte, 1982, vol. 115, p. 1509–1524.
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Article (Published version)
  • PID : unige:168219
ISSN of the journal0009-2940

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