Cyclisation of 3-(p-methylphenyl)propan-1-ol via its alkoxyl radical and aryl radical cation intermediates. A comparison of regioselectivities
Abstract
Evidence is presented that 3-(p-methylphenyl)propan-1-ol 5 undergoes competing 1,5- and 1,6-cyclisation via both its aryl radical cation 6 and alkoxyl radical 7 intermediates. Variations in both product yields and regioselectivities of cyclisation with pH are observed, with evidence of significant differences between the two intermediates.