Journal of Organic Chemistry p. 4914 - 4917 (1983)
Update date:2022-08-29
Topics:
Walling, Cheves
El-Taliawi, Gamil M.
Zhao, Chengxue
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.
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