The Radical Addition of Toluene to Fluorocyclobutenes

Abstract
Fluorine-containing cyclobutane derivatives, 1-benzyl-1,2,2,3,3,4,-hexafluorocyclobutane (1) and 1,5,6,6,7,7-hexafluorobenzo[2,3]bicyclo[3.2.0]hept-2-ene (2), were synthesized in one step by the radical reaction of toluene and hexafluorocyclobutene. On the other hand, a similar reaction of toluene and 1,2-dichlorotetrafluorocyclobutene gave no adduct, but a substituted product, 1-benzyl-2-chlorotetrafluorocyclobutene (4).