An Unusual Radical Fragmentation of 8a-Cycloalkenylmethyl Wieland-Miescher Ketones Mediated by Tri-n-butyltin Hydride

Article abstract of DOI:10.1016/S0040-4039(00)75858-8

The behaviour of tri-n-butyltin hydride in poly functional molecule like Wieland-Miescher ketones, was found to be very unusual, a remarkable difference in chemoselectivity was noticed in the reductive cyclisation of cycloalkenyl bromides, resulting in the remote generation of the bromocyclopentenyl-methyl radical by a homolytic C-C bond cleavage.