59719-22-1Relevant academic research and scientific papers
1,4-Di(1,2-di-tert-butyl-2-phenylethenyl)benzene and related twist- twist pi conjugated stilbene (PPV) systems
Gano, James E.,Kirschbaum, Kristin,Luzik Jr., Eddie D.,Sekher, Padmanabhan
, p. 6641 - 6644 (1998)
Twist-twist, pi conjugated, TTPC, systems are described. The twisted stilbene motif represented by 2,2,5,5-tetramethyl-3,4-diphenylhex-3-ene is extended to systems with five and seven perpendicular pi systems. UV spectra show extension of the chain imparts a regular red shift to the prominent π→π* transition. The shift is attenuated compared to planar pi conjugated systems. Extended TTPC systems occur as mixtures of atropisomers with very similar energies.
Enantioselective hydrogenation and transfer hydrogenation of bulky ketones catalysed by a ruthenium complex of a chiral tridentate ligand
Diaz-Valenzuela, M. Belen,Phillips, Scott D.,France, Marcia B.,Gunn, Mary E.,Clarke, Matthew L.
supporting information; experimental part, p. 1227 - 1232 (2009/08/10)
A study on the enantioselective hydrogenation of tertiary alkyl ketones catalysed by a novel class of tridentate-Ru complex is reported. In contrast to the extensively studied [RuCl2(diphos)(di-primary amine)] complexes, this new class of hydro
Novel synthesis of 4,5-diarylphenanthrenes via C2-C6 cyclization of benzannulated enyne-allenes
Li,Petersen,Wang
, p. 7804 - 7810 (2007/10/03)
A new synthetic pathway to the 4,5-diarylphenanthrenes 8 having a helical twist in their structures was developed. The synthetic sequence involves condensation of the diketone 5 with 2 equiv of the lithium acetylides derived from the diacetylenes 4 followed by protonation to produce the propargylic alcohols 6. Reduction of 6 with triethylsilane in the presence of trifluoroacetic acid furnished the tetraacetylenic hydrocarbons 7 in nearly quantitative yields. Treatment of 7 with potassium tertbutoxide under refluxing toluene at 110 °C for up to 10 h then furnished the 4,5-diarylphenanthrenes 8. Apparently, the transformation from 7 to 8 involves initial prototropic isomerizations to form the benzannulated enyne-allenes 9. Two subsequent formal intramolecular Diels-Alder reactions via the biradicals 10 and 12 derived from the C2-C6 cyclizations then led to 13, which in turn underwent tautomerizations to give 8. The structure of 8a was established by the X-ray structure analysis, showing that the two phenyl substituents are bent away from each other and the central aromatic system is severely distorted with a helical twist. The existence of a helical twist in 8 imposed by the aryl groups at the 4- and 5-positions was also revealed with a set of AB 1H NMR signals for the diastereotopic methylene hydrogens on the five-membered rings.
