Aryl tetrafluorosulfanyl compounds

1. A compound of the Formula (I):

wherein

X and X′ are independently selected from

wherein

represents the point of connection to SF 4 residue;

Y is selected from hydrogen and chlorine;

Ar and Ar′ are independently selected from aryl and heteroaryl, each optionally substituted by one or more substituents in addition to R 2 or R 2′ independently selected from halogen, nitro, —SH, trifluoromethyl, and C 1-4 hydrocarbyl, wherein one or more carbon atoms of the C 1-4 hydrocarbyl group may optionally be replaced by O, CO, or SO 2 ;

n and n′ are independently 0 or 1;

Ph ring is a phenyl ring optionally substituted by up to four substituents in addition to R 1 , independently selected from halogen, nitro, —SH, trifluoromethyl, and C 1-4 hydrocarbyl, wherein one or more carbon atoms of the C 1-4 hydrocarbyl group may optionally be replaced by O, CO, or SO 2 ;

R 1 , R 2 , and R 2′ are independently absent or selected from hydrogen, halogen, hydroxy, trifluoromethyl, pentafluorosulfanyl, cyano, nitro, carboxy, amino, mono- or di-C 1-4 hydrocarbylamino, carbocyclic and heterocyclic groups having from 3 to 12 ring members; and a group A-B wherein A is a bond, O, CO, Z 1 C(Z 2 ), C(Z 2 )Z 1 , Z 1 C(Z 2 )Z 1 , S, SO, SO 2 , NR c , SO 2 NR c or NR c SO 2 , and B is selected from hydrogen, carbocyclic and heterocyclic groups having from 3 to 12 ring members, and a C 1-8 hydrocarbyl group optionally substituted by one or more substituents selected from hydroxy, oxo, halogen, cyano, nitro, carboxy, amino, mono- or di-C 1-4 hydrocarbylamino, and carbocyclic and heterocyclic groups having from 3 to 12 ring members optionally substituted by one or more substituents selected from halogen, C 1-6 hydrocarbyl, C 1-6 hydrocarbyloxy, C 1-6 acyloxy, trifluoromethyl, trifluoromethoxy, and difluoromethoxy, and wherein one or more carbon atoms of the C 1-8 hydrocarbyl group may optionally be replaced by O, CO, S, SO, SO 2 , NR c , Z 1 C(Z 2 ), C(Z 2 )Z 1 or Z 1 C(Z 2 )Z 1 ; and R 1 may additionally be —SF 4 —X′—(Ar′) n′ —R 2′ ; with the provisos that (a) when X is

n is 0 and R 2 is A-B, where A is O; and (b) when X′ is

n′ is 0 and R 2′ is A-B, where A is O;

R c is selected from hydrogen and C 1-4 hydrocarbyl; and

Z 1 and Z 2 are independently selected from O, S, and NR c .

2. A compound according to claim 1 wherein R 1 , R 2 , and R 2′ are independently absent or selected from hydrogen, fluorine, chlorine, bromine, trifluoromethyl, pentafluorosulfanyl, cyano, nitro, carboxy, amino, mono- or di-C 1-4 hydrocarbylamino; and a group A-B wherein A is a bond, O, CO, C(═O)O, OC(═O), OC(═O)O, or NR c ; and R 1 may additionally be —SF 4 —X′—(Ar′) n′ —R 2′ .

3. A compound according to claim 2 wherein B is hydrogen or a C 1-8 hydrocarbyl group optionally substituted by one or more substituents selected from hydroxy, oxo, halogen, cyano, nitro, carboxy, amino, and carbocyclic and heterocyclic groups having from 3 to 6 ring members optionally substituted by one or more substituents selected from halogen, C 1-6 hydrocarbyl, C 1-6 hydrocarbyloxy, C 1-6 acyloxy, trifluoromethyl, trifluoromethoxy, and difluoromethoxy; and wherein one or more carbon atoms of the C 1-8 hydrocarbyl group may optionally be replaced by O, CO, S, SO, SO 2 , NR c , OC(═O), C(═O)O or OC(═O)O.

4. A compound according to claim 1 wherein R 1 , R 2 , and R 2′ are independently absent or selected from hydrogen, fluorine, chlorine, bromine, trifluoromethyl, cyano, nitro, carboxy, amino; and a group A-B wherein A is a bond, O, CO, C(═O)O, OC(═O), OC(═O)O, or NR c and B is hydrogen, a carbocyclic or heterocyclic group having from 3 to 6 ring members, or a C 1-8 hydrocarbyl group optionally substituted by one or more substituents selected from hydroxy, oxo, halogen, cyano, nitro, amino, or mono- or di-C 1-4 hydrocarbylamino, and wherein one or more carbon atoms of the C 1-8 hydrocarbyl group may optionally be replaced by O, CO, S, SO, SO 2 , NR c , OC(═O), C(═O)O or OC(═O)O; and R 1 may additionally be —SF 4 —X′—(Ar′) n′ —R 2′ .

5. A compound according to claim 1 wherein n is 1.

6. A compound according to claim 5 wherein Ar is phenyl.

7. A compound according to claim 1 wherein n is 1, n′ is 1, Ar is phenyl, and Ar′ is phenyl.

8. A compound according to claim 1 of formula (IA) or (IB):

wherein Ar is optionally substituted by up to three substituents in addition to R 2 , independently selected from halogen, nitro, trifluoromethyl, and C 1-4 hydrocarbyl.

9. A compound according to claim 1 wherein n is 0.

10. A compound according to claim 1 wherein R 1 and R 2 are independently selected from hydrogen, halogen, nitro, and an unsubstituted C 1-8 hydrocarbyl group, wherein one or more carbon atoms of the C 1-8 hydrocarbyl group may optionally be replaced by O, CO, S, SO, SO 2 , NR c , Z 1 C(Z 2 ), C(Z 2 )Z 1 or Z 1 C(Z 2 )Z 1 .

11. A compound according to claim 1 wherein the Ph ring is a phenyl ring substituted only by R 1 .

12. A compound according to claim 1 wherein the Ph ring is a phenyl ring substituted by R 1 and one or more additional substituents independently selected from halogen, nitro, —SH, trifluoromethyl, and C 1-4 hydrocarbyl, wherein one or more carbon atoms of the C 1-4 hydrocarbyl group may optionally be replaced by O, CO, or SO 2 .

13. A compound according to claim 12 wherein R 1 is not —SF 4 —X′—(Ar′) n′ —R 2′ .

14. A compound according to claim 1 wherein R 1 is attached para to the SF 4 residue on Ph.

15. A compound according to claim 1 wherein one of R 1 and R 2 is Z a , and the other is Z b , and wherein

Z a is selected from nitro, cyano, carboxy, and trifluoromethyl; and

Z b is selected from hydroxy, C 1-8 hydrocarbyloxy, and mono- or di-C 1-4 hydrocarbylamino.

16. A compound according to claim 1 of the Formula (I-i), (I-ii), (I-iii), or (I-iv):

wherein R 1 , R 2 , and R 2′ are independently selected from hydrogen, halogen, nitro, and a group A-B; and wherein R 1 may additionally be —SF 4 —X′—(Ar′) n′ —R 2′ .

17. A liquid crystal display (LCD) comprising a compound according to claim 1 .

18. A process for the preparation of a compound as defined in claim 1 , which process comprises:

the reaction of a compound of the formula:

with an alkene or alkyne compound of the formula:

wherein the reaction is carried out in the presence of a free radical initiator, and wherein Ph, Ar, n, R 1 , and R 2 are as defined in claim 1 , and optionally thereafter converting one compound of the Formula (I) into another compound of the Formula (I).

19. A process according to claim 18 wherein the free radical initiator is a trialkyl borane.

20. A process according to claim 18 wherein the reaction is carried out in the presence of a saturated hydrocarbon solvent.