288404-66-0Relevant academic research and scientific papers
Dual Gold-Catalyzed Three-Component Reaction: Efficient Synthesis of Indene-Fused Esters, Acids, and Lactones through Gold Vinylidene Intermediates
Yu, Congjun,Ma, Xiaodong,Chen, Bin,Tang, Bencan,Paton, Robert S.,Zhang, Guozhu
, p. 1561 - 1565 (2017/04/01)
A dual gold(I)-catalyzed three-component reaction was developed to prepare indene-fused carboxylic acid derivatives from diynes, alcohols, and pyridine N-oxides in both inter- and intramolecular fashions. The pyridine N-oxides were found to exhibit distinct selectivity unlike the α-oxo gold carbene intermediates in the well-developed gold-catalyzed oxidative functionalization of alkynes. Experimental studies and DFT calculations support double nucleophilic substitution of a gold vinylidene intermediate.
Deltoid versus Rhomboid: Controlling the Shape of Bis-ferrocene Macrocycles by the Bulkiness of the Substituents
Hoffmann, Viktor,Le Pleux, Lo?c,H?ussinger, Daniel,Unke, Oliver T.,Prescimone, Alessandro,Mayor, Marcel
, p. 858 - 866 (2017/04/21)
Precise structural control of heteroannularly disubstituted ferrocene (Fc) structures is very challenging as the high rotational mobility of the Fc unit allows a large conformational diversity. Herein we present the syntheses, characterization, and electr
Syntheses of Acetylenic Oligophenylene Macrocycles Based on a Novel Dewar Benzene Building Block Approach
Ohkita, Masakazu,Ando, Kohta,Suzuki, Takanori,Tsuji, Takashi
, p. 4385 - 4390 (2007/10/03)
A general synthetic approach to strained p-phenylene-based acetylenic macrocycles is described. A key feature in this approach is exploitation of Dewar benzene as an angular p-phenylene synthon. Thus, 1,4-acetal-bridged 2,5-dichloro(Dewar benzene) 5, prepared in four steps from dimethyl acetylenedicarboxylate and 1,2-dichloroethylene, is applied as such a building block in the syntheses of strained macrocycles 13 and anti-20. For the synthesis of 13, m-phenylene units are used as spacers and modified Eglington-Glaser coupling is applied for the macrocyclization step. For the synthesis of anti-20, on the other hand, o-phenylene units are used as spacers and Sonogashira coupling is applied for the macrocyclization step. Macrocycles 13 and anti-20 are characterized crystallographically, and their strained nature is reflected mainly in the deviation of the acetylene units from linearity; the C≡C-C angles range from 168.7(3)° to 179.9(3)° in 13 and from 168.0(5)° to 171.4(4)° in anti-20. Macrocycle 13 shows unique conformational property, namely, the p-phenylene units arranged in parallel in the rectangular framework rotate freely about the long axes, as evidenced by the 1H NMR studies. Macrocycle anti-20 exhibits a Stokes shift of 179 nm, which is exceptionally large for phenylacetylene macrocycles, presumably owing to the characteristic stacking structure.
