Unexpected switch in regioselectivity of tether-directed Bingel-type biscyclopropanations depending on the leaving groups at tethered active methylene moieties

Abstract

The regioselectivity of tether-directed Bingel-type biscyclopropanations of [60]fullerene was switched depending on the leaving groups at tethered active methylene moieties; the reactions of [60]fullerene with unhalogenated tethered bis(active methylene) derivatives/I₂ and with brominated derivatives in the presence of 1,7-diazabicyclo[5.4.0]undec-7-ene gave trans-4-adducts predominantly, while the reactions with chlorinated derivatives afforded equatorial-adducts almost exclusively.