254-03-5Relevant articles and documents
Iron-catalysed borylation of arenediazonium salts to give access to arylboron derivatives via aryl(amino)boranes at room temperature
Marciasini, Ludovic D.,Richy, Nicolas,Vaultier, Michel,Pucheault, Mathieu
, p. 1083 - 1088 (2013/05/21)
Complementary to previously described Miyaura borylation methods, a new access to boron derivatives via aryl(amino)boranes is described. Direct coupling between aryldiazonium salts and diisopropylaminoborane is catalysed by 0.1% ferrocene leading to the formation of a carbon-boron bond. The obtained aryl(amino)boranes could eventually then be transformed into boronic acids, boronates or borates. Copyright
o-Benzoquinone Methide: An Intermediate in the Gas-Phase Pyrolysis of Chroman
Paul, Gitendra C.,Gajewski, Joseph J.
, p. 5060 - 5062 (2007/10/02)
Gas-phase pyrolysis of chroman gives o-cresol, benzofuran, and styrene in a 4:2:1 ratio at 413 deg C.In the presence of 2-butene, a moderately stereospecific 4 + 2 reaction occurs with the likely intermediate, o-benzoquinone methide, 1.The addition of 2-butene increased the amount of reaction and decreased the extent of formation of benzofuran and styrene.Addition of hydrogen gas increased the amount of hydrodealkoxylation product, styrene, and gave more of its reduction product, ethylbenzene, at the expense of benzofuran.Only a slight increase in the amount of o-cresol was observed upon addition of hydrogen gas.No dehydrochroman was observed in the reactions, and pyrolysis of 4H- and 2H-benzopyran gave no o-cresol, but instead gave styrene, benzofuran, 1-indanone, and some chroman.
Oxidation of Arylalkanols by S2O82--CuII
Walling, Cheves,El-Taliawi, Gamil M.,Zhao, Chengxue
, p. 4914 - 4917 (2007/10/02)
Products of oxidation of a series of arylalkanols by S2O82--CuII in acetic acid and acetonitrile are consistent with initial oxidation to aryl radical cations followed by either loss of a benzylic proton or C-C bond scission and subsequent oxidation of intermediate benzylic radicals by CuII to final products. 1-Arylalkanols (ArCHOHR)react by both paths, C-C bond scission increasing with stability of the radical R.. 2-Arylalkanols (ArCH2CHOHR) give chiefly C-C bond scission to benzyl radicals and RCHO.The 3- and 4-arylalkanols undergo chiefly proton loss, and the resulting radicals are oxidized with cyclization to chromans and 2-phenylfurans, respectively, both of which may by oxidized in turn to further products.
