57196-50-6Relevant academic research and scientific papers
TfOH-Catalyzed Intramolecular Annulation of 2-(Aryl)-Phenyl-Substituted p-Quinone Methides under Continuous Flow: Total Syntheses of Selaginpulvilin i and Isoselagintamarlin A
Ahmad, Feroz,Anand, Ramasamy Vijaya,Fatma, Shaheen,Pandey, Rajat,Pankhade, Yogesh A.
, (2022/02/16)
In this article, we describe a convenient method to access 9-aryl fluorene derivatives through a TfOH-catalyzed intramolecular 1,6-conjugate arylation of 2-(aryl)-phenyl-substituted p-quinone methides (QMs) under continuous flow using the microreaction technique. This method was found to be very effective for most of the p-QMs, and the corresponding 9-aryl fluorene derivatives were obtained in moderate to excellent yields. Moreover, this protocol was further elaborated to the first total syntheses of selaginpulvilin I and isoselagintamarlin A.
Electroorganic Reactions. 31. Quinonemethide Radical-Anions and Dianoins: Their Cathodic Generation and Reactivity
Goulart, Marilia O. F.,Utley, James H. P.
, p. 2520 - 2525 (2007/10/02)
The cathodic reactions of a number of relatively stable quinonemethides have been examined in detail by cyclic voltammetry, controlled potential coulometry, and rigorous product analysis following preparative-scale electrolyses.The results of cyclic voltammetric experiments differ in some respects from those of earlier polarographic work.The lifetimes of the electrogenerated radical-anions and dianions, in the absence of added electrophile, are governed by steric hindrance.Hindered intermediates are relatively long-lived yet hydrogenate in the presence of proton donor and alkylate in the presence of methyl iodide.Less hindered analogue efficiently and rapidly dimerize, at carbon, with concomitant protonation or O-methylation depending on added electrophile.The ambident cathodically generated nucleophiles alkylate at both carbon and oxygen, and the competition is crucially dependent on the cation (Bu4N+ or Li+).Fuchsone 3 gives reduction products which vary with initial concentration and on the presence, or otherwise, of oxygen.Efficient reaction between oxygen and triarylmethyl radicals generated, e.g., from 3 has been demonstrated.
ELECTRO-ORGANIC REACTIONS. PART 32. ELECTROGENERATED BASES FROM QUINONEMETHIDES
Goulart, Marilia O. F.,Ling-Chung Sim K.,Utley, James H. P.
, p. 6081 - 6084 (2007/10/02)
The radical-anion of fuchsone (1), and the dianions of related quinonemethides, are generated at low cathodic potentials and act as bases in high yielding Wittig reactions; the phenolic product may be oxidatively reconverted into quinonemethide.
