Cao, Sheng published the artcileSubstituent Effects on Oxidation-Induced Formation of Quinone Methides from Arylboronic Ester Precursors, Application In Synthesis of 25240-59-9, the publication is Chemistry – A European Journal (2013), 19(27), 9050-9058, database is CAplus and MEDLINE.
A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N+Me3Br–) have been synthesized. The substituent effects on their reactivity with H2O2 and formation of quinone methide (QM) have been investigated. NMR spectroscopy and Et vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, resp. QMs were not generated during oxidative cleavage of the boronic esters but by subsequent transformation of the phenol products under physiol. conditions. The oxidative deboronation is facilitated by electron-withdrawing substituents, such as aromatic F, NO2, or benzylic N+Me3Br–, whereas electron-donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH3 or OMe group, or a good leaving group (Br), efficiently generate QMs under physiol. conditions. Finally, a quant. relationship between the structure and activity has been established for the arylboronic esters by using a Hammett plot. The reactivity of the arylboronic acids/esters and the inhibition or facilitation of QM formation can now be predictably adjusted. This adjustment is important as some applications may benefit and others may be limited by QM generation.
Chemistry – A European Journal published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Application In Synthesis of 25240-59-9.
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