Compound characterization data — Kuchukulla and Shibata, 2026

Ratnakar Reddy Kuchukulla, Norio Shibata. “Synthesis of novel 2-(tetrafluoro(1,2,2-trifluorovinyl)-λ⁶-sulfaneyl)aryls and their applications.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007669/v1

5-bromo-2-((2-chloro-1,2,2-trifluoroethyl)tetrafluoro-λ⁶-sulfaneyl)pyridine
Identifier	3a
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 8.60 (d, J = 2.3 Hz, 1H), 8.02 (dd, J = 8.6, 2.3 Hz, 1H), 7.66 (d, J = 8.7 Hz, 1H), 5.79 – 5.66 (m, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 166.0 (q, J = 28.4 Hz), 148.8, 141.2, 122.9 (td, J = 299.7, 28.1 Hz), 123.7, 122.7 (q, J = 4.4 Hz), 110.7 – 107.8 (m)
¹⁹F NMR (658 MHz, CDCl₃)	δ 45.8 (td, J = 12.2, 5.3 Hz), −61.4 (d, J = 187.8 Hz), −65.8 – −66.6 (m), −157.5 (dt, J = 43.1, 15.0 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₇H₄BrClF₇NSNa: 403.8722, found 403.8753
IR (KBr)	2924, 1149, 995, 776 cm⁻¹

2-((2-chloro-1,2,2-trifluoroethyl)tetrafluoro-λ⁶-sulfaneyl)-5-(trifluoromethyl)pyridine
Identifier	3b
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 8.84 (dt, J = 2.5, 0.8 Hz, 1H), 8.16 (dd, J = 8.6, 2.4 Hz, 1H), 7.91 (d, J = 8.5 Hz, 1H), 5.85 – 5.64 (m, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 169.5 (p, J = 28.8 Hz), 145.1, 136.2 (d, J = 3.6 Hz), 129.5 (q, J = 33.7 Hz), 122.7 (td, J = 299.1, 28.0 Hz), 122.4 (q, J = 273.5 Hz), 121.6 (t, J = 4.6 Hz), 109.2 (ddq, J = 252.1, 35.9, 30.9 Hz)
¹⁹F NMR (282 MHz, CDCl₃)	δ 45.01 (td, J = 11.8, 4.8 Hz), −61.61 (dp, J = 178.5, 12.8 Hz), −62.59, −66.42 (dp, J = 179.1, 13.0 Hz), −157.74 (dt, J = 42.7, 15.0 Hz)
HRMS (ESI)	[M−H]⁺: calculated for C₈H₅ClF₁₀NS: 371.9672, found 371.9681
IR (KBr)	2985, 1330, 1226, 1079, 648 cm⁻¹

2-((2-chloro-1,2,2-trifluoroethyl)tetrafluoro-λ⁶-sulfaneyl)-5-nitropyridine
Identifier	3c
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	80.6 – 81.8 °C
¹H NMR (300 MHz, CDCl₃)	δ 9.37 (d, J = 2.7 Hz, 1H), 8.75 – 8.63 (m, 1H), 8.01 (dd, J = 8.9, 2.7 Hz, 1H), 5.78 (ddtd, J = 42.7, 11.0, 4.8, 2.8 Hz, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 172.0 – 168.4 (m), 145.1, 143.6, 134.1, 122.7 (td, J = 299.5, 28.4 Hz), 122.3 (t, J = 4.6 Hz), 110.3 – 108.0 (m)
¹⁹F NMR (282 MHz, CDCl₃)	δ 45.74 (td, J = 12.2, 5.1 Hz), −59.97 – −63.44 (m), −66.50 (ddt, J = 179.2, 28.7, 12.2 Hz), −157.77 (dt, J = 43.0, 15.3 Hz)
HRMS (ESI)	[M−H]⁺: calculated for C₇H₃ClF₇N₂O₂S: 346.9492, found 346.9477
IR (KBr)	2993, 1359, 1151, 777 cm⁻¹

2-((2-chloro-1,2,2-trifluoroethyl)tetrafluoro-λ⁶-sulfaneyl)pyridine
Identifier	3d
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (300 MHz, CDCl₃)	δ 8.58 (dd, J = 4.6, 2.1 Hz, 1H), 7.98 – 7.85 (m, 1H), 7.77 (d, J = 8.3 Hz, 1H), 7.48 (t, J = 6.2 Hz, 1H), 5.94 – 5.54 (m, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 169.7 – 164.5 (m), 147.8, 147.8, 138.8, 126.6, 122.9 (td, J = 300.4, 27.7 Hz), 121.4, 109.3 (ddt, J = 254.0, 67.2, 33.7 Hz)
¹⁹F NMR (282 MHz, CDCl₃)	δ 44.48 (td, J = 11.9, 4.7 Hz), −61.08 (q, J = 12.5 Hz), −61.71 (q, J = 12.9 Hz), −65.97 (dt, J = 24.7, 11.7 Hz), −66.60 (dt, J = 24.4, 11.7 Hz), −157.63 (dt, J = 42.8, 14.8 Hz)
HRMS (ESI)	[M+H]⁺: calculated for C₇H₆ClF₇NS: 303.9798, found 303.9799
IR (KBr)	2920, 1224, 1055, 781 cm⁻¹

(2-chloro-1,2,2-trifluoroethyl)tetrafluoro(3-nitrophenyl)-λ⁶-sulfane
Identifier	3e
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 8.65 (t, J = 2.1 Hz, 1H), 8.36 (ddd, J = 8.2, 2.2, 0.9 Hz, 1H), 8.10 (ddd, J = 8.3, 2.2, 1.0 Hz, 1H), 7.68 (t, J = 8.2 Hz, 1H), 5.80 – 5.66 (m, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 157.2 (p, J = 24.1 Hz), 147.8, 131.7 (p, J = 5.0 Hz), 129.8, 126.0, 122.7 (td, J = 299.1, 28.1 Hz), 121.8 (p, J = 5.5 Hz), 109.8 (dp, J = 253.5, 67.3 Hz)
¹⁹F NMR (658 MHz, CDCl₃)	δ 55.69 (td, J = 12.3, 5.1 Hz), −61.58 (d, J = 182.1 Hz), −66.43 (ddt, J = 180.0, 26.3, 13.0 Hz), −156.60 (dt, J = 43.1, 15.2 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₈H₄ClF₇NO₂S: 345.9539, found 345.9546
IR (KBr)	2964, 1224, 1099, 783 cm⁻¹

(2-chloro-1,2,2-trifluoroethyl)tetrafluoro(4-fluorophenyl)-λ⁶-sulfane
Identifier	3f
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 7.81 – 7.73 (m, 2H), 7.14 – 7.06 (m, 2H), 5.73 – 5.60 (m, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 163.4 (d, J = 252.8 Hz), 153.0 (p, J = 23.1 Hz), 128.3 (dq, J = 10.2, 5.2 Hz), 122.9 (td, J = 300.0, 28.3 Hz), 117.5 – 116.1 (m), 115.4 (d, J = 23.1 Hz), 109.9 (ddt, J = 252.4, 66.9, 33.7 Hz)
¹⁹F NMR (658 MHz, CDCl₃)	δ 56.34 (td, J = 11.9, 4.9 Hz), −61.38 (d, J = 171.8 Hz), −66.36 (dtd, J = 178.2, 11.6, 3.7 Hz), −107.86 (tt, J = 8.4, 4.8 Hz), −156.41 – −156.57 (m)
HRMS (ESI)	[M−H]⁺: calculated for C₈H₄ClF₈S: 318.9594, found 318.9608
IR (KBr)	2919, 1245, 1054, 775 cm⁻¹

(2-chloro-1,2,2-trifluoroethyl)tetrafluoro(4-nitrophenyl)-λ⁶-sulfane
Identifier	3g
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	77.0 – 77.3 °C
¹H NMR (700 MHz, CDCl₃)	δ 8.31 (d, J = 8.9 Hz, 2H), 7.99 (d, J = 9.3 Hz, 2H), 5.78 – 5.68 (m, 1H)
¹³C NMR (126 MHz, CDCl₃)	δ 160.6 (d, J = 23.2 Hz), 148.7, 123.9, 111.5 – 109.7 (m), 109.6 – 107.7 (m)
¹⁹F NMR (658 MHz, CDCl₃)	δ 54.79 (td, J = 5.3, 12.4 Hz, 4F), −62.19 (d, J = 188.1 Hz, 1F), −67.07 (d, J = 178.9 Hz, 1F), −157.25 (dt, J = 15.1, 43.2 Hz, 1F)
HRMS (ESI)	[M−H]⁺: calculated for C₈H₅ClF₇NO₂S: 369.9515, found 369.9503
IR (KBr)	3122, 1531, 1353, 1229, 1155, 991, 859, 778, 746, 645 cm⁻¹

(2-chloro-1,2,2-trifluoroethyl)(4-chlorophenyl)tetrafluoro-λ⁶-sulfane
Identifier	3h
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 7.74 – 7.66 (m, 2H), 7.39 (s, 2H), 5.76 – 5.61 (m, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 155.4 (p, J = 22.2 Hz), 137.3, 128.8 (d, J = 6.2 Hz), 127.3 (p, J = 5.1 Hz), 124.9 – 120.8 (m), 109.9 (ddt, J = 252.2, 66.0, 33.3 Hz)
¹⁹F NMR (658 MHz, CDCl₃)	δ 55.71 (td, J = 11.9, 4.8 Hz), −59.11 – −63.01 (m), −65.40 – −68.68 (m), −156.58 (dt, J = 42.9, 14.8 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₈H₅Cl₂F₇NaS: 358.9275, found 358.9257
IR (KBr)	1478, 1153, 985, 779 cm⁻¹

(2-chloro-1,2,2-trifluoroethyl)tetrafluoro(p-tolyl)-λ⁶-sulfane
Identifier	3i
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 7.64 (d, J = 8.7 Hz, 2H), 7.21 (d, J = 8.5 Hz, 2H), 5.67 (ddtd, J = 42.8, 11.7, 4.7, 2.8 Hz, 1H), 2.38 (s, 3H)
¹³C NMR (176 MHz, CDCl₃)	δ 155.0 (p, J = 21.2 Hz), 141.9, 141.6, 129.1, 129.0, 128.8, 125.7 (p, J = 5.0 Hz), 123.1 (td, J = 299.3, 27.9 Hz), 111.1 – 108.8 (m), 21.1
¹⁹F NMR (658 MHz, CDCl₃)	δ 55.52 (td, J = 11.9, 4.8 Hz), −61.22 (d, J = 175.7 Hz), −66.05 – −66.45 (m), −156.51 (dt, J = 42.8, 14.7 Hz)
HRMS (ESI)	[M+H]⁺: calculated for C₉H₉ClF₇S: 317.0002, found 317.0009
IR (KBr)	1497, 1228, 1153, 993, 701 cm⁻¹

tetrafluoro(2-fluorophenyl)(1,2,2-trifluorovinyl)-λ⁶-sulfane
Identifier	3j
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 7.77 (ddd, J = 8.4, 6.8, 1.6 Hz, 1H), 7.46 (tdd, J = 8.4, 4.5, 1.6 Hz, 1H), 7.23 – 7.14 (m, 2H), 5.82 – 5.62 (m, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 155.6 (d, J = 259.8 Hz), 143.1 (td, J = 22.7, 10.7 Hz), 133.5 (d, J = 8.9 Hz), 133.2 (d, J = 9.1 Hz), 128.5 (p, J = 5.2 Hz), 123.8 (d, J = 3.8 Hz), 118.1 (d, J = 4.5 Hz), 117.9 (d, J = 23.9 Hz), 110.9 – 108.6 (m)
¹⁹F NMR (658 MHz, CDCl₃)	δ 60.00 (dtd, J = 24.4, 11.8, 4.8 Hz), −61.16 – −61.64 (m), −66.28 (ddtd, J = 178.6, 23.1, 11.5, 5.6 Hz), −107.22 (tdddd, J = 30.1, 25.1, 18.5, 11.6, 5.1 Hz), −157.48 (dt, J = 42.7, 14.9 Hz)
HRMS (ESI)	[M−H]⁺: calculated for C₈H₄ClF₈S: 318.9594, found 318.9601
IR (KBr)	1595, 1487, 1242, 1152, 987, 784 cm⁻¹

(2-chloro-1,2,2-trifluoroethyl)tetrafluoro(phenyl)-λ⁶-sulfane
Identifier	3k
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 7.80 – 7.74 (m, 2H), 7.51 – 7.38 (m, 3H), 5.76 – 5.62 (m, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 158.7 – 155.9 (m), 137.3, 131.2, 128.6 (d, J = 20.0 Hz), 127.4, 125.9 (d, J = 8.9 Hz), 125.0 – 121.0 (m), 109.8 (ddd, J = 251.5, 67.0, 33.8 Hz)
¹⁹F NMR (658 MHz, CDCl₃)	δ 54.96 (td, J = 12.6, 5.5 Hz), −61.25 (d, J = 191.2 Hz), −65.98 – −66.57 (m), −156.58 (ddt, J = 50.6, 22.3, 11.1 Hz)
HRMS (ESI)	[M−H]⁺: calculated for C₈H₅ClF₇S: 300.9689, found 300.9701
IR (KBr)	1225, 1152, 985, 777 cm⁻¹

5-bromo-2-(tetrafluoro(1,2,2-trifluorovinyl)-λ⁶-sulfaneyl)pyridine
Identifier	4a
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	77.9 – 78.7 °C
¹H NMR (700 MHz, CDCl₃)	δ 8.61 (dd, J = 2.4, 0.7 Hz, 1H), 8.02 (ddd, J = 8.6, 2.2, 1.1 Hz, 1H), 7.66 (d, J = 8.7 Hz, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 166.5 – 166.1 (m), 151.3 (td, J = 292.8, 40.8 Hz), 148.8, 141.2, 123.6, 122.6 (t, J = 4.6 Hz)
¹⁹F NMR (658 MHz, CDCl₃)	δ 52.95 – 52.90 (m), −99.42 (ddq, J = 114.5, 52.9, 13.9 Hz), −102.20 (ddp, J = 55.5, 53.3, 11.8 Hz), −156.22 – −156.54 (m)
HRMS (ESI)	[M+H]⁺: calculated for C₇H₂BrF₇NS: 343.8980, found 343.8987
IR (KBr)	3089, 1784, 1333, 1232, 778

2-(tetrafluoro(1,2,2-trifluorovinyl)-λ⁶-sulfaneyl)-5-(trifluoromethyl)pyridine
Identifier	4b
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	53.1 – 54.6 °C
¹H NMR (700 MHz, CDCl₃)	δ 8.84 (d, J = 2.3 Hz, 1H), 8.16 (dd, J = 8.7, 2.6 Hz, 1H), 7.92 (d, J = 8.6 Hz, 2H)
¹⁹F NMR (658 MHz, CDCl₃)	δ 52.16 (td, J = 13.1, 5.3 Hz), −62.46, −99.12 (ddp, J = 55.7, 52.7, 14.1 Hz), −101.54 – −101.80 (m), −156.49 – −156.79 (m)
¹³C NMR (176 MHz, CDCl₃)	δ 169.8 (p, J = 28.9 Hz), 145.2, 136.3, 129.5 (q, J = 34.2 Hz), 151.4 (td, J = 300.3, 38.5 Hz), 122.4 (q, J = 273.2 Hz), 121.6 – 121.5 (m)
HRMS (ESI)	[M−H]⁺: calculated for C₈H₂F₁₀NS: 333.9748, found 333.9730
IR (KBr)	2963, 1733, 1261, 1096, 801
IR (KBr)	1758, 1329, 1075, 810, 732 cm⁻¹

5-nitro-2-(tetrafluoro(1,2,2-trifluorovinyl)-λ⁶-sulfaneyl)pyridine
Identifier	4c
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	63.8 – 65.2 °C
¹H NMR (700 MHz, CDCl₃)	δ 9.37 (dd, J = 2.6, 0.6 Hz, 1H), 8.69 (dd, J = 8.9, 2.6 Hz, 1H), 8.00 (d, J = 8.9 Hz, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 170.48 (p, J = 27.2 Hz), 152.29 (td, J = 291.8, 36.4 Hz)145.19, 143.65, 134.12, 122.37
¹⁹F NMR (658 MHz, CDCl₃)	δ 52.95 – 52.80 (m), −98.83 (ddt, J = 115.1, 51.6, 14.0 Hz), −100.97 – −101.23 (m), −156.84 (ddq, J = 115.3, 55.7, 5.4 Hz)
HRMS (ESI)	[M+H]⁺: calculated for C₇H₄F₇N₂O₂SH: 312.9882, found 312.9879
IR (KBr)	3113, 1782, 1361, 1231, 772

2-(tetrafluoro(1,2,2-trifluorovinyl)-λ⁶-sulfaneyl)pyridine
Identifier	4d
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	39 – 40 °C
¹H NMR (700 MHz, CDCl₃)	δ 8.56 (dd, J = 5.2, 1.9 Hz, 1H), 7.90 (tdd, J = 8.2, 2.0, 1.0 Hz, 1H), 7.76 (d, J = 8.3 Hz, 1H), 7.47 (ddd, J = 7.4, 4.6, 0.8 Hz, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 168.1 (p, J = 27.3 Hz), 153.3 – 149.0 (m), 147.8, 143.0 (dd, J = 282.8, 27.4 Hz), 138.7, 126.6, 121.3 (t, J = 4.6 Hz)
¹⁹F NMR (658 MHz, CDCl₃)	δ 51.71 (ddd, J = 13.8, 11.7, 5.0 Hz), −99.70 (ddq, J = 114.3, 54.2, 13.9 Hz), −102.77 (tp, J = 54.7, 11.8 Hz), −156.04 – −156.35 (m)
HRMS (ESI)	[M+H]⁺: calculated for C₇H₅F₇NS: 268.0031, found 268.0036
IR (KBr)	2963, 1729, 1469, 1071, 636 cm⁻¹

tetrafluoro(3-nitrophenyl)(1,2,2-trifluorovinyl)-λ⁶-sulfane
Identifier	4e
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	75.2 – 76.8 °C
¹H NMR (700 MHz, CDCl₃)	δ 8.66 (t, J = 2.1 Hz, 1H), 8.37 (ddd, J = 8.2, 2.1, 0.9 Hz, 1H), 8.11 (ddd, J = 8.3, 2.2, 1.0 Hz, 1H), 7.68 (t, J = 8.2 Hz, 1H)
¹³C NMR (176 MHz, CDCl₃)	δ 157.54 (p, J = 24.4 Hz), 151.23 (td, J = 293.0, 40.4 Hz), 145.11 – 141.03 (m), 143.13 (d, J = 255.7 Hz), 131.76 (p, J = 5.0 Hz), 129.83, 126.01, 121.86 (p, J = 5.3 Hz)
¹⁹F NMR peak annotations (658 MHz, CDCl₃)	δ 62.97, 62.96, 62.95, 62.95, 62.94, 62.94, 62.93, 62.92; −99.13, −99.15, −99.18, −99.19, −99.20, −99.21, −99.23, −99.26, −99.28, −99.29, −99.31, −99.33, −99.35, −99.37, −99.37, −99.39, −99.41, −99.43, −99.45; −102.00, −102.02, −102.03, −102.05, −102.06, −102.06, −102.08, −102.08, −102.10, −102.10, −102.11, −102.12, −102.13, −102.14, −102.14, −102.16, −102.18, −102.20, −102.22; −155.64, −155.65, −155.66, −155.67, −155.67, −155.73, −155.74, −155.74, −155.75, −155.76, −155.82, −155.83, −155.83, −155.84, −155.85, −155.90, −155.91, −155.92, −155.93, −155.93
HRMS (ESI)	[M+Na]⁺: calculated for C₈H₄F₇NO₂NaS: 333.9749, found 333.9734
IR (KBr)	3132, 1779, 1534, 1353, 880, 781 cm⁻¹

(4-chlorophenyl)tetrafluoro(1,2,2-trifluorovinyl)-λ⁶-sulfane
Identifier	4f
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 7.78 – 7.62 (m, 2H), 7.40 (d, J = 8.5 Hz, 2H)
¹³C NMR (126 MHz, CDCl₃)	δ 155.64 (p, J = 22.7 Hz), 151.10 (td, J = 291.9, 39.4 Hz), 145.76 – 141.32 (m), 137.23, 128.66, 127.32
¹⁹F NMR (658 MHz, CDCl₃)	δ 63.08 – 62.95 (m), −100.05 (ddt, J = 114.3, 54.6, 14.0 Hz), −103.37 (tp, J = 55.2, 12.0 Hz), −155.33 (ddp, J = 114.3, 55.6, 4.8 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₈H₄F₇ClNaS: 322.9508, found 322.9507
IR (KBr)	1777, 1333, 1232, 705 cm⁻¹

tetrafluoro(p-tolyl)(1,2,2-trifluorovinyl)-λ⁶-sulfane
Identifier	4g
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	32 – 33 °C
¹H NMR (700 MHz, CDCl₃)	δ 7.66 (d, J = 8.7 Hz, 2H), 7.22 (d, J = 7.6 Hz, 2H), 2.39 (s, 3H)
¹³C NMR (176 MHz, CDCl₃)	δ 155.38 (p, J = 21.2 Hz), 153.02 – 149.22 (m), 145.46 – 142.39 (m), 141.62, 129.04, 125.73 (p, J = 4.9 Hz), 21.08
¹⁹F NMR (658 MHz, CDCl₃)	δ 62.83 (td, J = 13.3, 4.8 Hz), −100.60 (ddq, J = 113.6, 56.1, 14.0 Hz), −104.33 (tp, J = 55.8, 12.0 Hz), −154.82 – −155.21 (m)
HRMS (ESI)	[M−H]⁺: calculated for C₉H₆F₇S: 279.0078, found 279.0066
IR (KBr)	1778, 1337, 1228, 790 cm⁻¹

tetrafluoro(2-fluorophenyl)(1,2,2-trifluorovinyl)-λ⁶-sulfane
Identifier	4h
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
¹H NMR (700 MHz, CDCl₃)	δ 7.78 (ddd, J = 8.4, 6.8, 1.6 Hz, 1H), 7.47 (tdd, J = 8.5, 4.4, 1.6 Hz, 1H), 7.22 – 7.16 (m, 2H)
¹³C NMR (176 MHz, CDCl₃)	δ 155.6 (d, J = 259.9 Hz), 153.3 – 148.9 (m), 144.7 – 142.1 (m), 133.2 (d, J = 8.9 Hz), 128.5 (p, J = 5.1 Hz), 123.8 (d, J = 3.9 Hz), 117.9 (d, J = 23.8 Hz)
¹⁹F NMR (658 MHz, CDCl₃)	δ 62.94 (ddd, J = 14.0, 12.1, 5.1 Hz), −99.29 (ddq, J = 114.9, 52.8, 14.1 Hz), −102.10 (ddp, J = 56.0, 52.8, 11.9 Hz), −155.79 (ddt, J = 114.8, 56.0, 5.0 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₈H₄F₈NaS: 306.9804, found 306.9793; [M−H]⁺: calculated for C₈H₃F₈S: 282.9828, found 282.9824
IR (KBr)	2374, 1753, 1527, 1355, 1075, 801 cm⁻¹

tetrafluoro(4-nitrophenyl)(1,2,2-trifluorovinyl)-λ⁶-sulfane
Identifier	4i
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	142 – 143 °C
¹H NMR (700 MHz, CDCl₃)	δ 8.31 (d, J = 8.8 Hz, 2H), 7.98 (d, J = 9.2 Hz, 2H)
¹³C NMR (176 MHz, CDCl₃)	δ 161.16 (p, J = 23.5 Hz), 153.25 – 149.27 (m), 148.84, 144.50 – 141.80 (m), 127.51 (p, J = 5.0 Hz), 123.98
¹⁹F NMR (658 MHz, CDCl₃)	δ 62.64 (td, J = 13.1, 5.0 Hz), −99.13 – −99.49 (m), −101.95 – −102.21 (m), −155.58 – −156.00 (m)
HRMS (ESI)	[M+Na]⁺: calculated for C₈H₄F₇NO₂NaS: 333.9749, found 333.9736
IR (KBr)	1779, 1543, 1339, 1229, 789 cm⁻¹

2-((2-((4-(tert-butyl)phenyl)thio)-1,2,2-trifluoroethyl)tetrafluoro-λ⁶-sulfaneyl)-5-(trifluoromethyl)pyridine
Identifier	5a
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	98.8 – 100.3 °C
¹H NMR (700 MHz, CDCl₃)	δ 8.81 (dt, J = 2.4, 0.8 Hz, 1H), 8.12 (dd, J = 8.7, 2.3 Hz, 1H), 7.89 (d, J = 8.5 Hz, 1H), 7.61 – 7.58 (m, 2H), 7.45 – 7.41 (m, 2H), 5.65 – 5.53 (m, 1H), 1.33 (s, 9H)
¹³C NMR (176 MHz, CDCl₃)	δ 170.12 (p, J = 29.2 Hz), 154.53, 145.12, 136.17, 129.26 (q, J = 34.1 Hz), 126.73, 121.72, 120.99, 110.83 – 108.56 (m), 34.98, 31.23
¹⁹F NMR (658 MHz, CDCl₃)	δ 45.73 (td, J = 12.3, 5.0 Hz), −62.44, −82.43 (ddt, J = 229.2, 20.7, 12.8 Hz), −90.25 (d, J = 231.9 Hz), −156.35 (ddd, J = 42.7, 21.1, 17.6 Hz)
HRMS (ESI)	[M+H]⁺: calculated for C₁₈H₁₈F₁₀NS₂: 502.0721, found 502.0722
IR (KBr)	2965, 1392, 1124, 783

2-(tetrafluoro(1,2,2-trifluoro-3,3-dimethylbutyl)-λ⁶-sulfaneyl)-5-(trifluoromethyl)pyridine
Identifier	5b
NMR reporting reference	Chemical shifts (δ) are expressed in ppm downfield from TMS (δ = 0.00 ppm) and CDCl₃ (δ = 7.26 ppm) for ¹H NMR, CDCl₃ (δ = 77.16 ppm) for ¹³C NMR and ¹⁹F NMR
Melting point	129.5 – 130.8 °C
¹H NMR (700 MHz, CDCl₃)	δ 8.84 – 8.81 (m, 1H), 8.13 (dd, J = 8.6, 2.3 Hz, 1H), 7.92 (d, J = 8.6 Hz, 1H), 5.77 (ddt, J = 42.6, 22.1, 4.6 Hz, 1H), 1.19 (s, 9H)
¹³C NMR (176 MHz, CDCl₃)	δ 171.77 – 169.49 (m), 145.04, 136.06, 128.97 (t, J = 33.7 Hz), 123.39, 121.86 – 121.72 (m), 113.02 – 108.30 (m), 40.13 (t, J = 22.0 Hz), 24.34
¹⁹F NMR (658 MHz, CDCl₃)	δ 44.99 (ddt, J = 17.5, 13.4, 3.6 Hz), −62.43, −115.15 – −119.18 (m), −124.34 – −128.37 (m), −156.20 (dd, J = 42.5, 17.4 Hz)
HRMS (ESI)	[M+Na]⁺: calculated for C₁₂H₁₃F₁₀NSNa: 416.0507, found 416.0517
IR (KBr)	2968, 1386, 1329, 773