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US 2004/0106827 A1Published application
Method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic and aromatic compounds
AssigneeUniversity of Florida
InventorsWilliam R. Dolbier JR., Samia Ait-Mohand
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Abstract
The subject invention provides convenient, regiospecific and highly stereoselective addition of SF5Cl in high yield to a variety of alkenes and alkynes.
Claims13
A method of making pentafluorosulfanyl substituted compounds comprising the steps of:
- a) contacting a hexane solution comprising one or more compounds comprising one or more functional groups selected from the group consisting of substituted or unsubstituted aliphatic groups, substituted or unsubstituted aromatic groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted alkene groups, substituted or unsubstituted alkyne groups, substituted or unsubstituted styrene groups, disubstituted alkene groups (e.g., 2,2-disubstituted alkenes), substituted or unsubstituted non-terminal alkene groups, substituted or unsubstituted non-terminal alkyne groups, cyclohexene groups, substituted cyclohexene groups, cyclohexadiene groups, substituted cyclohexadiene groups, and combinations of such functional groups, or derivatives of the aforementioned functional groups, with a SF5Cl hexane solution;
- b) adding one or more catalyst(s)/initiator(s) selected from the group consisting of dialkylboranes, trialkylboranes, 9-borabicyclo[3.3.1] nonane, and mixtures thereof;
- and
- c) allowing the reaction of said compounds and said SF5CL solution to proceed under conditions suitable for the addition of pentafluorosulfanyl substituents to said compounds.
1 more element
A method of making pentafluorosulfanyl benzene comprising the steps of:
- a) mixing 4,5-dichloro-1-cyclohexane, CH2Cl2, SF5Cl, and a catalyst selected from the group consisting of dialkylboranes, trialkylboranes, 9-borabicyclo[3.3.1] nonane, and mixtures thereof;
- b) evaporating the solvent from the mixture of step a) and recovering the product produced thereby;
- c) contacting the product obtained in step b) with a solution of sodium ethoxide (NaOEt);
- d) adding water to the solution of step c) and extracting said solution;
- e) washing the extract of step d) and drying the extract over a dessicant;
- f) allowing solvent evaporation from the extract of step e);
- and
- g) recovering pentafluorosulfanylbenzene from the extract of step f).
5 more elements
Dependencies are inferred from the claim text.