60043-12-1Relevant academic research and scientific papers
Carbonylative, Catalytic Deoxygenation of 2,3-Disubstituted Epoxides with Inversion of Stereochemistry: An Alternative Alkene Isomerization Method
Lamb, Jessica R.,Hubbell, Aran K.,MacMillan, Samantha N.,Coates, Geoffrey W.
supporting information, p. 8029 - 8035 (2020/05/01)
Reactions facilitating inversion of alkene stereochemistry are rare, sought-after transformations in the field of modern organic synthesis. Although a number of isomerization reactions exist, most methods require specific, highly activated substrates to achieve appreciable conversion without side product formation. Motivated by stereoinvertive epoxide carbonylation reactions, we developed a two-step epoxidation/deoxygenation process that results in overall inversion of alkene stereochemistry. Unlike most deoxygenation systems, carbon monoxide was used as the terminal reductant, preventing difficult postreaction separations, given the gaseous nature of the resulting carbon dioxide byproduct. Various alkyl-substituted cis- A nd trans-epoxides can be reduced to trans- A nd cis-alkenes, respectively, in >99:1 stereospecificity and up to 95% yield, providing an alternative to traditional, direct isomerization approaches.
Tritylated alkyl aryl ethers
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Paragraph 0012; 0013; 0014; 0015, (2016/10/09)
A compound having formula (Ph3C)mAr(R1)j(OR2)n, wherein Ph represents a phenyl group, Ar is an aromatic ring system having from six to twenty carbon atoms, R1 and R2 independently are C1-C18 alkyl or C4-C18 heteroalkyl, m is one or two, j is an integer from one to four and n is an integer from one to three.
Controlling the catalytic aerobic oxidation of phenols
Esguerra, Kenneth Virgel N.,Fall, Yacoub,Petitjean, Laurène,Lumb, Jean-Philip
supporting information, p. 7662 - 7668 (2014/06/10)
The oxidation of phenols is the subject of extensive investigation, but there are few catalytic aerobic examples that are chemo- and regioselective. Here we describe conditions for the ortho-oxygenation or oxidative coupling of phenols under copper (Cu)-catalyzed aerobic conditions that give rise to ortho-quinones, biphenols or benzoxepines. We demonstrate that each product class can be accessed selectively by the appropriate choice of Cu(I) salt, amine ligand, desiccant and reaction temperature. In addition, we evaluate the effects of substituents on the phenol and demonstrate their influence on selectivity between ortho-oxygenation and oxidative coupling pathways. These results create an important precedent of catalyst control in the catalytic aerobic oxidation of phenols and set the stage for future development of catalytic systems and mechanistic investigations.
Synthesis of salicylaldehydes bearing bulky substituents in the positions 3 and 5
Kochnev,Oleynik,Oleynik,Ivanchev,Tolstikov
, p. 1125 - 1129 (2008/09/17)
Reaction of 2,4-disubstituted phenols with paraformaldehyde in the presence of SnCl4 and 2,6-lutidine afforded a number of new salicylaldehydes, containing bulky substituents (tert-butyl, 1-phenylethyl, 1-(4-tert- butylphenyl)ethyl, α-cumyl, and trityl) in the positions 3 and 5.
