An unusual radical fragmentation of 8a-cycloalkenylmethyl Wieland-Miescher ketones mediated by tri-n-butyltin hydride

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 CC bond cleavage. © 1994.