Oxymetallation. Part 17. t-Butyl peroxymercuriation and subsequent demercuriation of phenylcyclopropane
Abstract
Phenylcyclopropane reacts with mercury(II) trifluoroacetate and two equivalents of t-butyl hydroperoxide in dichloromethane to give a mixture of PhCH(OOBut)CH2CH2HgO2CCF3(47%) and PhCH(O2CCF3)CH2CH2HgO2CCF3(36%). Reduction with alkaline sodium borohydride converts this mixture into one of PhCH(OOBut)Et and PhCH (OH)Et, from which the pure peroxide (19% overall) has been isolated by silica chromatography. Brominolysis of the corresponding mixture of organomercury bromides followed by silica chromatography has afforded PhCH(OOBut)CH2CH2Br (29% overall).