User:OrganoMetallurgy/Drafts/Pentafluorosulfanyl

The pentafluorosulfanyl functional group, -SF5, also known the sulfur pentafluoride group, is a strong electron withdrawing group, which is stable under a variety of harsh conditions. Its presence on a molecule confers increased lipophilicity. The sulfur has octahedral geometry around it.

Properties
Slightly smaller than a tert-butyl group, larger than a trifluoromethyl group. Octahedral geometry around sulfur. Strongly electron withdrawing. Confers increased lipophilicy to molecules

Synthesis
Radical addition of SF5X compounds, typically SF5Cl or SF5Br, to unsaturated compounds. Addition reactions involving SF5Cl or SF5Br can be catalysed by triethylborane.

Fluorination of suitable sulfur containing precursors. (Using chorine and alkali metal fluorides) need to check.

As of July 2017, there are no commercial applications of any molecules containing the pentafluorosulfanyl group. However there is pentafluorosulfanyl group is promising from the point of view of the development of new drugs and other bioactive molecules due to its unusual combination of properties of high polarity and high lipophilicity. Materials science Liquid crystals

temp
Sometimes called pentafluorosulfur or sulfur pentafluoride group.

Sometimes called a super-trifluoromethyl group due to increased electronegativity, lipophilicity, and chemical stablity, as compared to the trifluoromethyl group