Synthesis of diamantanedicarboxylic acids with the carboxy groups bonded at tertiary carbon atoms

Abstract

The preparation of diamantanedicarboxylic acids with the carboxy groups at the tertiary carbon atoms of the diamantane skeleton is described. The procedure comprises bromination or oxidation of 1- and 4-diamantanecarboxylic acid and Koch-Haaf carboxylation of the reaction products. Of the four diamantanedicarboxylic acids synthesized, two - 1,4- and 1,7-diamantanedicarboxylic acids - have not been so far described.

Abundant naphthenic acids in oil sands process‐affected water: studies by synthesis, derivatisation and two‐dimensional gas chromatography/high‐resolution mass spectrometry

“…The mass spectra of the methyl esters of some isomers of (F) hydroxydiamantane carboxylic acids have already been published. [24,25] Of these, none was identical to those observed for the current unknowns in the OSPW samples (Figs. 3(A)-3(C)) but, in addition to the molecular ion (m/z 262), the spectra of some of the previously synthesised hydroxydiamantane carboxylic acids (methyl esters) did contain a base peak at m/z 203 (e.g.…”

“…This would be expected for the methyl esters of O 3 ‐containing acids, such as isomers of hydroxydiamantane carboxylic acids. The mass spectra of the methyl esters of some isomers of hydroxydiamantane carboxylic acids have already been published . Of these, none was identical to those observed for the current unknowns in the OSPW samples (Figs.…”

“…Diamantane‐1‐ and 4‐carboxylic acids were converted separately into mixtures of bromodiamantane‐1‐ or 4‐carboxylic acid isomers by non‐ionic bromination as reported previously . Bromination of diamantane‐1‐carboxylic acid produced three of the five theoretically possible isomers.…”

“…Syntheses of hydroxydiamantane carboxylic acids were performed as described previously. [24,25] Briefly, authentic 1or 4-diamantane carboxylic acid was brominated (Br 2 , 70 C for 1-2 h) and the subsequent bromoacids hydrolysed (70% HNO 3 , 70 C for 12 h) to the respective hydroxydiamantane carboxylic acids. Hydroxycarboxylic acids and OSPW extracts were derivatised by refluxing with BF 3 -methanol, BF 3 -trideuteriomethanol or treatment with BSTFA.…”

Selective Preparation of Diamondoid Fluorides[1]

“…The brominated compounds 9b, 10b, 11b, 12b, 13b, and 14b were prepared by the procedure of Gund et al [34] Also the compounds 9c, 10c, 11c, 12c, 13c, 16a, 17a, 18a, 19a, 20a, 21a, 22, 31, 34, 37, and 39 were prepared using literature procedures. [11,12,15,37,42] Procedures for the Preparation of Fluorinated Diamondoids 9a-21a…”