60462-24-0Relevant articles and documents
Enantioselective synthesis of (: R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane
Houston, Sevan D.,Chalmers, Benjamin A.,Savage, G. Paul,Williams, Craig M.
, p. 1067 - 1070 (2019)
The first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed. The key step was a telescoped Strecker reaction using (S)-2-amino-2-phenylethanol as a chiral auxiliary. Exploration of an alternative synthetic approach resulted in unprecedented cubane C-H insertion.
Synthesis, High-Resolution Infrared Spectroscopy, and Vibrational Structure of Cubane, C8H8
Boudon,Lamy,Dugue-Boyé,Pirali,Gruet,D'Accolti,Fusco,Annese,Alikhani
, p. 4418 - 4428 (2016/07/11)
Carbon-cage molecules have generated a considerable interest from both experimental and theoretical points of view. We recently performed a high-resolution study of adamantane (C10H16), the smallest hydrocarbon cage belonging to the diamandoid family (Pirali, O.; et al. J. Chem. Phys. 2012, 136, 024310). There exist another family of hydrocarbon cages with additional interesting chemical properties: the so-called platonic hydrocarbons that comprise dodecahedrane (C20H20) and cubane (C8H8). Both possess C-C bond angles that deviate from the tetrahedral angle (109.8°) of the sp3 hybridized form of carbon. This generates a considerable strain in the molecule. We report a new wide-range high-resolution study of the infrared spectrum of cubane. The sample was synthesized in Bari upon decarboxylation of 1,4-cubanedicarboxylic acid thanks to the improved synthesis of literature. Several spectra have been recorded at the AILES beamline of the SOLEIL synchrotron facility. They cover the 600-3200 cm-1 region. Besides the three infrared-active fundamentals (ν10, ν11, and ν12), we could record many combination bands, all of them displaying a well-resolved octahedral rotational structure. We present here a preliminary analysis of some of the recorded bands, performed thanks the SPVIEW and XTDS software, based on the tensorial formalism developed in the Dijon group. A comparison with ab initio calculations, allowing to identify some combination bands, is also presented.
