Reactions of nucleophiles with perfluoro[2.2]paracyclophane.
The aromatic rings of perfluoro[2.2]paracyclophane are extremely reactive with respect to nucleophilic substitution reactions. This paper emphasizes products of monosubstitution by hydroxide, alkoxide, thiolate, enolate, and amine nucleophiles. All reactions appear to proceed via S(N)Ar mechanisms; reactivity issues are discussed including the effect of substituents on reactivity and regiochemistry of substitution.
Zhang
Lianhao
L
Department of Chemistry, P.O. Box 117200, University of Florida, Gainesville, Florida 32611-7200, USA.
Ogawa
Katsu
K
Ghiviriga
Ion
I
Dolbier
William R
WR