Reactions of Organic Pentafluorosulfanyl-containing Compounds

The utility of pentafluorosulfanyl (SF5)-containing compounds has been limited because the chemistry has not been fully explored. While significant attention has been focused on the incorporation of fluorine in C-F bonds, or the introduction of a trifluoromethyl (CF3) groups, our attention has been focused on the SF5 group. The SF5 group has a similar electron withdrawing effect as the CF3 group yet the SF5 group is significantly more lipophilic. Combining these properties results in the proclivity of SF5-containing arenes to undergo displacement reactions. The hydrophobicity of the SF5-group was used to direct the conformation of SF5-containing peptides. The profound dipole associated with pentafluorosulfanylation has been successfully used to direct the stereochemistry of the Staudinger reaction. The greater steric demand of the SF5 group relative to the CF3 group has dramatically effected the conformation of small molecules by encumbering rotational freedom. The influence of the SF5-group on the reactions of alkanes, alkenes, alkynes, arenes and various functional groups is reviewed below.