81453-27-2Relevant academic research and scientific papers
Iodobenzene and m-chloroperbenzoic acid mediated oxidative dearomatization of phenols
Taneja, Neha,Peddinti, Rama Krishna
, p. 3958 - 3963 (2016)
Oxidative dearomatization of 2- and 4-substituted phenols to their corresponding benzoquinone monoketals by catalytic amount of iodobenzene, and m-CPBA as a co-oxidant has been achieved via in situ generation of PhIO2, a hypervalent iodine(V) s
Coupling of Quinone Monoacetals with Vinyl Ethers Effected by Tetrabutylammonium Triflate: Regiocontrolled Synthesis of 2-Oxygenated Dihydrobenzofurans
Kamitanaka, Tohru,Tsunoda, Yusuke,Fujita, Yuriko,Dohi, Toshifumi,Kita, Yasuyuki
supporting information, p. 9025 - 9029 (2021/11/24)
The synthesis of 2-oxygenated dihydrobenzofurans involving the [3 + 2] coupling of quinone monoacetals with vinyl ethers has been realized by tetrabutylammonium triflate catalysis. The reaction involves a new activation method of the acetal moiety in quinone monoacetals under acid-free conditions affording the highly oxygenated dihydrobenzofurans. This new activation mode was achieved by using the triflate anion catalyst for stabilization of the highly reactive cationic intermediate.
Direct synthesis of anilines and nitrosobenzenes from phenols
St Amant,Frazier,Newmeyer,Fruehauf,Read De Alaniz
supporting information, p. 5520 - 5524 (2016/07/06)
A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.
Lewis acid catalyzed [3+2] coupling of indoles with quinone monoacetals or quinone imine ketal
Shu, Chang,Liao, Li-Hua,Liao, Yi-Jun,Hu, Xiao-Yan,Zhang, Yong-Hong,Yuan, Wei-Cheng,Zhang, Xiao-Mei
supporting information, p. 4467 - 4471 (2014/08/05)
The one-pot synthesis of benzofuroindolines and tetrahydroindolo[2,3-b] indoles was accomplished through a mild and concise [3+2] coupling of indoles and quinone monoacetals or quinone imine ketal promoted by a Lewis acid. A wide variety of benzofuroindolines and tetrahydroindolo[2,3-b]indoles were prepared in moderate to good yields. Copyright
A Mechanistic Study of the Thermal Disproportionation Reaction of Quinone Monoketals
Capparelli, Michael P.,Swenton, John S.
, p. 5360 - 5364 (2007/10/02)
Thermolysis of quinone monoketals 1a-d at 180 deg C leads to disproportionation to the p-alkoxyphenols 2a-d and the carbonyl compounds derived from the alcohol moiety of the ketal.The thermolysis of 4,4-dimethoxy-2,5-cyclohexadienone (1a) followed first-order kinetics, and the rate of reaction decreased by a factor of 3.6 when the methoxy groups were replaced with methoxy-d3 groups.The suggested mechanism for the reaction involves reversible dissociation of 1a into a p-methoxyphenoxy-methoxy radical pair, followed by rate-controlling hydrogen atom transfer to give p-methoxyphenol and formaldehyde.Although 1a has a half-life of about 4 h at 180 deg C, the monoethylene glycol ketal of benzoquinone was recovered in > 90percent yield after heating for 24 h at the same temperature.Finally, acid-catalysed exchange of 3,3,6,6-tetramethoxy-1,4-cyclohexadiene with alcohols furnished a convenient route to quinone bisketals not obtainable in good yield via anodic oxidation.
