90965-63-2Relevant academic research and scientific papers
Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents
Xiao, Xiao,Greenwood, Nathaniel S.,Wengryniuk, Sarah E.
supporting information, p. 16181 - 16187 (2019/11/05)
Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.
Associative chemosensing by fluorescent macrocycle-dye complexes-a versatile enzyme assay platform beyond indicator displacement
Biedermann, Frank,Hathazi, Denisa,Nau, Werner M.
supporting information, p. 4977 - 4980 (2015/03/30)
A label-free in situ method to monitor reactions in real time by using fluorescent supramolecular chemosensors based on cucurbit[8]uril is presented. It allows sensing of enzymatic activity, inhibitor and activator screening, and analyte detection with unprecedented versatility and high sensitivity.
Rapid halogen substitution and dibenzodioxin formation during tyrosinase-catalyzed oxidation of 4-halocatechols
Stratford, Michael R. L.,Riley, Patrick A.,Ramsden, Christopher A.
experimental part, p. 350 - 356 (2012/04/23)
4-Fluoro-1,2-benzoquinone, generated by tyrosinase oxidation of 4-fluorocatechol in aqueous buffer, rapidly undergoes substitution by O-nucleophiles (water or catechols) with release of fluoride. 4-Chloro- and 4-bromocatechol behave similarly. The reactions, which have toxicological implications, have been monitored by spectrophotometry and HPLC/MS, and intermediate and final products, including dibenzodioxins, identified.
Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family
Lin, David W.,Masuda, Takeshi,Biskup, Moritz B.,Nelson, Jonathan D.,Baran, Phil S.
, p. 1013 - 1030 (2011/04/15)
A sweeping structural revision of the sarcodonin natural product family (published structures 1a-13a) is proposed after extensive studies aimed at their chemical synthesis. Key features of revised structure 1b include replacement of the N,N-dioxide moiety with an oxime, ring-opening of the central diketopiperazine, and transposition of the terphenyl wing from the 1β-2β position of 1a to the 2β-3β position of 1b. This structure revision arose from the serendipitous synthesis of a benzodioxane aminal (44) whose structure was unambiguously determined by X-ray crystallography and whose spectral properties bore considerable resemblance to the published data for the sarcodonins. A versatile new method for O-arylation of hydroxamic acids is also reported herein, as well as a manganese(III)- mediated α-oxidation of hydroxamic acids to aminals.
Kinetics and Mechanism of Oxidation of Acetanilide and para-Substituted Acetanilides by HClO4-Phenyliodosyl Acetate System
Radhakrishnamurti, P. S.,Sasmal, B. M.,Patnaik, D. P.
, p. 106 - 108 (2007/10/02)
Oxidation of acetanilide and p-methyl-, p-chloro-, p-bromo- and p-nitro-acetanilides by phenyliodosyl acetate (PIA) in the presence of HClO4 in aqueous medium is first order in and fractional order each in and .Increase in percentage of HOAc in the solvent mixture increases the rate.A probable reaction mechanism and rate law consistent with it have been discussed.
