63194-75-2Relevant academic research and scientific papers
Chemoselective oxidative generation of ortho-quinone methides and tandem transformations
Ishihara, Kazuaki,Kondo, Ryutaro,Nishioka, Kohei,Uyanik, Muhammet
, p. 353 - 362 (2020/04/09)
ortho-Quinone methides are useful transient synthetic intermediates in organic synthesis. These species are most often generated in situ by the acid- or base-mediated transformation of phenols that have been pre-functionalized at a benzylic position, or by biomimetic oxidation of the corresponding ortho-alkylphenols with metal oxidants or transition-metal complexes. Here we describe a method for the transition-metal-free oxidative generation of o-QMs from ortho-alkylarenols, using hypoiodite catalysis under nearly neutral conditions, which can then be applied in one-pot tandem reactions. This method for the chemoselective oxidative generation of ortho-quinone methides may prove superior to previous methods with respect to environmental issues and scope, and can be applied to various tandem reactions such as inter- or intramolecular [4 + 2] cycloaddition, oxa-6π-electrocyclization, conjugate addition and spiroepoxidation. [Figure not available: see fulltext.].
Organophotoredox-catalyzed intermolecular Oxa-[4+2] cycloaddition reactions
Tanaka, Kenta,Omata, Daichi,Asada, Yosuke,Hoshino, Yujiro,Honda, Kiyoshi
, p. 10669 - 10678 (2019/08/22)
An intermolecular oxa-[4+2] cycloaddition reaction promoted by a thioxanthylium photoredox catalyst under irradiation with green light has been developed. The reaction of ortho-quinone methides with styrenes smoothly affords the desired cycloadducts. Espe
Electrochemical synthesis of chroman and euglobal skeletons via cycloaddition reaction of o-quinone methides and alkenes
Chiba, Kazuhiro,Sonoyama, Junko,Tada, Masahiro
, p. 1435 - 1443 (2007/10/03)
Euglobal skeletons were synthesized by the intermolecular cycloaddition reaction of terpenes and o-quinone methides generated in situ by electrochemical oxidation. In a two-phase reaction medium composed of hexane-lithium perchlorate/nitromethane, 2-[1-(p
Novel Generation of o-Quinone Methides on the Basis of Lewis Acid Catalyzed 1,4-Dethiolation of o-(1-(Alkylthio)alkyl)phenols
Inoue, Tsutomu,Inoue, Seiichi,Sato, Kikumasa
, p. 55 - 58 (2007/10/02)
The treatment of o-(1-(alkylthio)alkyl)phenols with Lewis acid resulted in the formation of o-quinone methides by the novel 1,4-dethiolation process, which, being activated with Lewis acid, reacted in situ with various dienophiles in the manner of Diels-Alder reaction in high efficiency. o-Quinone allide, provided from o-(1-(alkylthio)allyl)phenol, also behaved as heterodienes.
A New Generation of o-Quinone Methides from o-(1-(Alkylthio)alkyl)phenols under Mild Conditions
Inoue, Tsutomu,Inoue, Seiichi,Sato, Kikumasa
, p. 653 - 656 (2007/10/02)
o-(1-(Alkylthio)alkyl)phenols are converted into o-quinone methides in good yield by treatment with silver oxide under mild conditions.Since the methides tend to prefer (E) configuration, cis-4-alkyl-2-alkoxychromans are exclusively obtained as a result o
o-Quinone Methides. Part 3. X-Ray Crystal Structure and Reactivity of a Stable o-Quinone Methide in the E-Configuration.
Arduini, Arturo,Pochini, Andrea,Ungaro, Rocco,Domiano, Paolo
, p. 1391 - 1396 (2007/10/02)
An X-ray crystal structure determination of 6-(4-methoxybenzylidene)-3,4-methylenedioxycyclohexa-2,4-dienone (2a), allows an E-configuration to be assigned to this stable o-quinone methide.The reactions of (2a) with magnesium phenolates and ethyl vinyl et
