13135-02-9Relevant academic research and scientific papers
Ru-Catalyzed δ-Arylation of para-Quninone Methides with Aryl Diazonium Salts to Synthesize Fuchsones
Dai, Lei,Mao, Kaimin,Zhang, Ge,Wang, Chang,Liu, Yun,Rong, Liangce,Zhang, Jinpeng
, p. 7238 - 7246 (2020/06/05)
A novel reaction mode and efficient ruthenium-catalyzed Matsuda-Heck-type arylation of para-quinone methides (p-QMs) with aryl diazonium salts has been developed for the synthesis of symmetrical or unsymmetrical δ,δ′-diaryl quinone methides (fuchsones). Aryl groups are introduced at the δ-position of p-QMs via tandem olefin insertion reaction/β-H elimination processes. This reaction features advantages such as mild and green conditions, broad reactant scope, and high yields.
Chiral and racemic tetramorphs of 2,6-di-t-butylditolylfuchsone
Nath, Naba K.,Nilapwar, Sanjay,Nangia, Ashwini
experimental part, p. 1613 - 1625 (2012/07/01)
The title molecule 4-(α,α-ditolylmethylene)-2,6-di-t-butyl-1,4- benzoquinone (abbreviated as di-t-butylditolylfuchsone and numbered 2-t-Bu) serendipitously afforded four concomitant polymorphs during routine purification by column chromatography in the same solvent elution fraction. Polymorph I crystallized in chiral space group P21. Polymorphs II, III, and IV crystallized in centrosymmetric space groups P21/n, Pbca, and C2/c, respectively. The role of bulky t-Bu groups for crystallization in the chiral space group is discussed for 2,6-ditolyl and 2,6-diphenyl fuchsones. α,α-Diphenylmethylene-2,6-di-t-butyl-1,4-benzoquinone (di-t-butyldiphenylfuchsone, 1-t-Bu) crystallized in P21 (one polymorph) and P21/c (two polymorphs) space groups. Unfavorable steric repulsions due to bulky t-Bu groups result in voids in the crystal structures of centrosymmetric polymorphs II and III. Phase transformation of racemic structure II to III and finally to chiral polymorph I was monitored by thermal microscopy and differential scanning calorimetry. X-ray diffraction confirmed the phase transformation to be a single-crystal-to-single-crystal event. The chiral polymorph I is the stable modification in the tetramorphic system. Several randomly picked single crystals of 2-t-Bu polymorph I had the same absolute chirality by circular dichroism spectroscopy. A new molecule capable of exhibiting conformational chirality via atropisomerism is identified.
2,6-di-tert-butyl-4-diarylmethylene-2,5-cyclohexadiene-1-thiones. First isolable unannelated thioquinone methides
Suzuki, Riho,Kurata, Hiroyuki,Kawase, Takeshi,Masaji, Oda
, p. 571 - 572 (2007/10/03)
Unannelated thioquinone methides were first synthesized as labile but isolable substances with aid of steric protection; they exhibit higher dipolar properties and stronger electron affinity than the corresponding quinone methides.
