Addition reaction of halogens to vinyl(pentafluorocyclopropanes): competition between a radical addition and an electrophilic addition.
Vinylpentafluorocyclopropanes 1 react with I(2) to give the (Z)-1,5-adduct 2, whereas 1 reacts with Cl(2), Br(2) or I-Cl to produce (Z)-1,5-adduct 3 predominantly along with small amounts of 1,2-adduct 4, which are formed by a radical mechanism and an ionic mechanism, respectively.
Yang
Zhen-Yu
ZY
DuPont Central Research and Development, Experimental Station, P.O. Box 80328, Wilmington, Delaware 19880-0328, USA. zhenyu.yang-1@usa.dupont.com