142337-65-3Relevant academic research and scientific papers
Bismuth(III) triflate catalyzed tandem esterification–Fries–oxa-Michael route to 4-chromanones
Meraz, Kevin,Gnanasekaran, Krishna Kumar,Thing, Rup,Bunce, Richard A.
, p. 5057 - 5061 (2016/11/02)
An efficient tandem reaction approach is described to prepare 4-chromanones from electron-rich phenols and 3,3-dimethylacrylic acid or trans-crotonic acid in boiling toluene using 20?mol?% bismuth(III) triflate as the catalyst. The reaction is also successful from the corresponding aryl esters of each of these acids under the same conditions. The procedure is convenient to perform, and 25–90% yields of products are realized following chromatography. A range of substrates is included (14 substrates for each acid) to help define the scope of the process. Additional experiments are reported, which confirm that the sequence of events involves (1) esterification, (2) Fries rearrangement and (3) oxa-Michael ring closure.
ON THE REACTION OF SUBSTITUTED PHENOLS AND 3-METHYLBUT-2-ENOIC ACID. A COMPARATIVE STUDY
Seboek, Peter,Jekoe, Jozsef,Timar, Tibor,Jaszberenyi, Joseph Cs.
, p. 2099 - 2114 (2007/10/02)
A systematic and comparative study of the reaction of a series of substituted phenols and 3-methylbut-2-enoic acid in zinc chloride/phosphorus oxychloride and aluminum chloride/phosphorus oxychloride reveals that the formation of phenolic esters and 2,2-dimethyl-4-chromanones is strongly influenced by the substituents, their popsition on the aromatic ring of the starting phenols.Based on our study, a mixed Friedel-Crafts and Fries rearrangement mechanism is in operation in these reactions.
On the synthesis of substituted 2,2-dimethyl1-4-chromanones and related compounds
Seboek, Peter,Jekoe, Jozsef,Timar, Tibor,Jaszberenyi, Joseph Cs.
, p. 2791 - 2794 (2007/10/02)
A systematic study of the reaction of a series of monosubstituted phenols 3 and 3-methylbut-2-enoic acid 4 in phosphorus oxychloride/zinc chloride revealed that the formation of 4-chromanones was strongly infuenced by the substituents and their position on the aromatic ring of the starting phenols.
