79654-37-8Relevant academic research and scientific papers
Iron-catalysed 1,2-aryl migration of tertiary azides
Wei, Kaijie,Yang, Tonghao,Chen, Qing,Liang, Siyu,Yu, Wei
supporting information, p. 11685 - 11688 (2020/10/19)
1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.
Sodium-Ketyl Radical Anions by Reverse Pinacol Reaction and Their Coupling with Iodoarenes
Tang, Xinjun,Studer, Armido
supporting information, p. 4448 - 4450 (2016/11/07)
Transition-metal-free C-C bond formation between aryl iodides and pinacols is presented. Pinacols are readily transformed by deprotonation with NaH to their Na-pinacolates. C-C-bond homolysis at room temperature generates in situ the corresponding Na-ketyl radical anions which react with various aryl iodides in a homolytic aromatic substitution reaction to form tertiary Na-alcoholates. Protonation eventually provides tertiary alcohols in an unprecedented route.
Palladium-catalyzed arylation of α,α-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls
Terao, Yoshito,Wakui, Hiroyuki,Nomoto, Michiyo,Satoh, Tetsuya,Miura, Masahiro,Nomura, Masakatsu
, p. 5236 - 5243 (2007/10/03)
The palladium-catalyzed arylation of α,α-disubstituted arylmethanols with aryl halides proceeds not only via C-H bond cleavage at the ortho-position, but also via cleavage of the sp2-sp3 C-C bond with the liberation of ketones (β-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C-C or C-H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides.
Hydrogen Bonding in Diphenylmethanols, RCPh2OH: Structures of Monomeric (4-Biphenyl)diphenylmethanol and Diphenyl(2-pyridyl)methanol, Dimeric 1,1,3-Triphenylpropyn-1-ol, Trimeric 2-Methyl-1,1-diphenylpropan-1-ol, Tetrameric Diphenyl(2-thienyl)methanol, Hexameric Bis(pentafluorophenyl)...
Ferguson, George,Carroll, Christopher D.,Glidewell, Christopher,Zakaria, Choudhury M.,Lough, Alan J.
, p. 367 - 377 (2007/10/02)
(4-Biphenyl)diphenylmethanol (1), C25H20O, orthorhombic, P212121, a = 8.3580(11), b = 13.8976(17), c = 15.5915(12) Angstroem, Z = 4, R = 0.032 for 1146 observations 3?(I)>: the structure contains isolated monomers with no hydrogen bonding.Diphenyl(2-pyridyl)methanol (2), C18H15NO, monoclinic, P21/c, a = 8.1899(8), b = 14.855(2), c = 11.6069(15) Angstroem, β = 96.344(8) deg, Z = 4, R = 0.049 for 879 observations 3?(I)>: the structure consists of isolated monomers in which the intramolecular O-H...N hydrogen-bond motif has graph set S(5). 1,1,3-Triphenylpropyn-1-ol (3), C21H16O, monoclinic, P21/c, a = 5.9794 (12), b = 9.953(3), c = 26.420(3) Angstroem, β = 91.365(12) deg, Z = 4, R = 0.039 for 971 observations 2?(I)>: the structure contains centrosymmetric dimers held together by O-H...?(arene) hydrogen bonds involving one of the phenyl groups, rather than the propargyl group. 2-Methyl-1,1-diphenylpropan-1-ol (4), C16H18O, trigonal, P31c, a = 13.9232(17), c = 12.0200(19) Angstroem, Z = 6, R = 0.031 for 763 observations 3?(I)>: the structure consists of cyclic hydrogen-bonded trimers with crystallographic threefold symmetry and disordered hydroxyl H atoms in a motif with graph set R33(6): the O...O distance in the trimers is 2.864(7) Angstroem.Diphenyl(2-thienyl)methanol (5), C17H14OS, rhombohedral, R, a = 19.20(1), c = 26.48(1) Angstroem, Z = 24; this compound is isomorphous and isostructural with triphenylmethanol, Ph3COH, and forms hydrogen-bonded tetrahedral tetramers.Bis(pentafluorophenyl)methanol (6), C13H2F10O, rhombohedral, R, a = 26.113(3), c = 9.788(3) Angstroem (at 293 K), R = 0.068 for 1214 observations 2?(I)>; a = 26.006(4), c = 9.5941(11) Angstroem (at 173 K), R = 0.072 for 1889 observations 2?(I)>, Z = 18; the structure consits of coaxial stacks of cyclic hydrogen-bonded hexamers, each of symmetry, and with a hydrogen-bond motif of graph set R66(12).Within the hexamers, the molecules are disordered over two orientations in the ratio 0.779(3):0.221(3) at 293 K and 0.776(2):0.224(2) at 173 K: the O...O distance is 2.702(4) Angstroem at 293 K and 2.683(4) Angstroem at 173 K.Diphenylmethanol (7), C13H12O, orthorhombic, P22121, a = 5.1300(10), b = 18.650(5), c = 21.168(6) Angstroem, Z = 8, R = 0.035 for 1487 observations 3?(I)>: there are two molecules in the asymmetric unit and the molecules are linked by hydrogen bonds into spiral chains having graph set C(4) and lying parallel to the a-axis; the O...O distances within the chains are 2.826(3) and 2.878(3) Angstroem.
Photochemical reactions of Thienyl-, Bithienyl-, Terthienyl- and Thienylaroyl-methanols
Krishnaswamy, N. R.,Kumar, Ch. Siva Sai Kamana,Prasanna, S.
, p. 1801 - 1830 (2007/10/02)
Photochemical reactions of some thienyl-, bithienyl-, terthienyl- and thienylaroyl-methanols were studied in the neat state as well as in solvents like methanol and benzene.The terthienylmethanols were found to be susceptible to photo-sensitized oxidation which was inhibited by singlet oxygen quenchers.The photoproducts were isolated, characterised by spectroscopic methods and in some cases by synthesis.
The Tris(2-thienyl)methyl Cation Problem. A Nuclear Magnetic Resonance Spectroscopic Study
Abarca, Belen,Asensio, Gregorio,Ballesteros, Rafael,Varea, Teresa
, p. 3224 - 3229 (2007/10/02)
A series of homologues of the trityl cation obtained by total or partial substitution of the phenyl rings for 2- or 3-thienyl groups has been studied by 1H and 13C NMR.In general, the spectral parameters found follow the expected trends.However, a most unexpected effect is found in the transformation of tris(2-thienyl)carbinol (1d) into tris(2-thienyl)methyl cation (2d) , since the increase of the total chemical shift (ΔΣδ) associated with the ionization is as low as 105 ppm.To account for this observation, several hypotheses are discussed including the possibility of through-space charge delocalization by the three sulfur atoms and the interaction of the thiophene rings in an alternate conformation.
