3238
N. Stellenboom et al. / Tetrahedron 66 (2010) 3228–3241
(1H, ddd, J¼8.3, 7.7, 1.5 Hz), 7.01 (1H, dd, J¼8.3, 1.5 Hz), 6.89 (1H,
td, J¼7.7, 1.5 Hz), 6.42 (1H, br s), 2.77 (2H, t, J¼7.3 Hz), 1.75 (2H,
sext, J¼7.3 Hz), 0.99 (3H, t, J¼7.3 Hz); 13C NMR (100.6 MHz,
CDCl3) dC: 156.6, 134.8, 131.9, 121.1, 120.8, 115.9, 40.4, 21.9, 13.0;
HRMS (EI) m/z calcd (Mþ) for C9H12OS2 200.0330, found
200.0325.
119.3, 110.2, 41.3, 22.0, 12.9; HRMS (ESI) m/z calcd (MþþH) for
C10H12NOS2 226.0360, found 226.0352.
3.6.12. Entry 12: 2-benzothiazolyl 1-Propyl disulfide37. Yield
0.587 g, 90%, as a colourless semi-solid; IR (CH2Cl2): nmax 500 (S–
S) cmꢀ1; 1H NMR (400 MHz, CDCl3) dH: 7.88 (1H, dd, J¼7.6, 1.2 Hz),
7.81 (1H, dd, J¼7.6, 1.2 Hz), 7.44 (1H, td, J¼7.6, 1.2 Hz), 7.34 (1H, td,
J¼7.6, 1.2 Hz), 2.96 (2H, t, J¼7.3 Hz), 1.81 (2H, sext, J¼7.3 Hz), 1.05
(3H, t, J¼7.3 Hz); 13C NMR (100.6 MHz, CDCl3) dC: 173.2,155.2,135.9,
126.2, 124.5, 122.1, 121.1, 41.5, 22.4, 13.0; HRMS (ESI) m/z calcd
(MþþH) for C10H12NS3 242.0132, found 242.0121.
3.6.5. Entry 5: 1-dodecyl 2-hydroxyphenyl disulfide. Yield 0.802 g,
91%, as a yellow oil; IR (CH2Cl2): nmax 3428 (OH), 500 (S–S) cmꢀ1; 1H
NMR (300 MHz, CDCl3) dH: 7.49 (1H, dd, J¼7.5, 1.4 Hz), 7.30 (1H,
ddd, J¼8.2, 7.5, 1.4 Hz), 7.00 (1H, dd, J¼8.2, 1.4 Hz), 6.88 (1H, td,
J¼7.5, 1.4 Hz), 6.38 (1H, br s), 2.76 (2H, t, J¼7.4 Hz), 1.69 (2H, quint,
J¼7.3 Hz), 1.34 (2H, m), 1.26 (16H, m), 0.88 (3H, t, J¼6.6 Hz); 13C
NMR (75.5 MHz, CDCl3) dC: 156.6, 134.9, 131.9, 121.1, 120.8, 115.9,
38.5, 31.9, 29.7, 29.6, 29.5, 29.4, 29.3, 29.1, 28.5, 28.4, 22.7, 14.1;
HRMS (EI) m/z calcd (Mþ) for C18H30OS2 326.1738, found 326.1746.
3.6.13. Entry 13: p-methoxyphenyl 3,3,4,4,5,5,6,6,6-nonafluoro-1-
hexyl disulfide. Yield 0.609 g, 54%, as a clear oil; IR (CH2Cl2): nmax
1265 (C–F), 499 (S–S) cmꢀ1; 1H NMR (300 MHz, CDCl3) dH: 7.48 (2H,
d, J¼8.9 Hz), 6.88 (2H, d, J¼8.9 Hz), 3.82 (3H, s), 2.89 (2H, m), 2.54
(2H, m); 13C NMR (100.6 MHz, CDCl3) dC: 160.3, 132.9, 127.1, 114.9,
3.6.6. Entry 6: p-aminophenyl 1-propyl disulfide. Yield 0.345 g, 64%,
as a dark-coloured oil; IR (CHCl3): nmax 3370, 3209 (NH), 490 (S–
S) cmꢀ1; 1H NMR (300 MHz, CDCl3) dH: 7.35 (2H, d, J¼8.4 Hz), 6.62
(2H, d, J¼8.4 Hz), 3.70 (2H, br s), 2.71 (2H, t, J¼7.4 Hz),1.71 (2H, sext,
55.3, 31.4 (t, JC–F¼22.1 Hz), 28.5; 19F NMR (376.3 MHz, CDCl3) dF
:
ꢀ81.5, ꢀ114.4 and ꢀ114.9, ꢀ124.8, ꢀ126.4; HRMS (EI) m/z calcd
(Mþ) for C13H11F9OS2 418.0108, found 418.0103.
J¼7.4 Hz), 0.96 (3H, t, J¼7.4 Hz); 13C NMR (75.5 MHz, CDCl3) dC
:
3.6.14. Entry 14: 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-
1-decyl p-tolyl disulfide. Yield 1.072 g, 66%, as a yellow solid; IR
146.7, 132.7, 125.5, 115.5, 40.7, 22.0, 13.1; HRMS (EI) m/z calcd (Mþ)
for C9H13NS2 199.0489, found 199.0482.
(CH2Cl2): nmax 1265 (C–F), 499 (S–S) cmꢀ1 1H NMR (400 MHz,
;
CDCl3) dH: 7.45 (2H, d, J¼8.0 Hz), 7.17 (2H, d, J¼8.0 Hz), 2.91 (2H, m),
2.53 (2H, m), 2.37 (3H, s); 13C NMR (100.6 MHz, CDCl3) dC: 138.1,
132.9, 130.0, 129.6, 31.5 (t, JC–F¼22.1 Hz), 28.8, 21.0; 19F NMR
(376.3 MHz, CDCl3) dF: ꢀ81.2, ꢀ114.2, ꢀ122.1, ꢀ122.3, ꢀ122.3,
ꢀ123.1, ꢀ123.8, ꢀ126.5; HRMS (EI) m/z calcd (Mþ) for C17H11F17S2
602.0031, found 602.0022; Found: C 33.88%, H 1.89%, S 10.54%;
C17H11F17S2 requires C 33.10%, H 1.84%, S 10.64%.
3.6.7. Entry 7: tert-butyl o-methoxycarbonylphenyl disulfide35. Yield
0.622 g, 90%, as a clear oil; IR (CHCl3) nmax 1708 (C]O), 487 (S–
S) cmꢀ1
;
1H NMR (400 MHz, CDCl3) dH: 8.22 (1H, dd, J¼8.2 Hz and
1.3 Hz), 7.97 (1H, dd, J¼8.2 Hz and 1.3 Hz), 7.49 (1H, ddd, J¼8.2 Hz,
7.5 Hz and 1.3 Hz), 7.19 (1H, ddd, J¼8.2 Hz, 7.5 Hz and 1.3 Hz), 3.94
(3H, s), 1.32 (9H, s); 13C NMR (75.5 MHz, CDCl3) dC: 166.8, 143.0,
132.2, 131.1, 127.1, 126.4, 124.9, 52.1, 49.2, 30.0; HRMS (EI) m/z calcd
(Mþ) for C12H16O2S2 256.0592, found 256.0597.
3.6.15. Entry 15: 3,3,4,4,5,5,6,6,6-nonafluorohexyl 2-hydroxyphenyl
disulfide. Yield 0.698 g, 64%, as a yellow solid; IR (CH2Cl2): nmax
3.6.8. Entry 8: 1-hexyl p-nitrophenyl disulfide. Yield 0.615 g, 84%, as
3472 (OH), 1265 (C–F), 499 (S–S) cmꢀ1 1H NMR (400 MHz, CDCl3)
;
a pale-yellow oil; IR (neat): nmax 1515, 1340 (NO2), 499 (S–S) cmꢀ1
;
dH: 7.48 (1H, dd, J¼7.6, 1.5 Hz), 7.36 (1H, ddd, J¼8.4, 7.6, 1.5 Hz), 7.04
(1H, dd, J¼8.4, 1.5 Hz), 6.92 (1H, td, J¼7.6, 1.5 Hz), 6.24 (1H, br s),
2.96, (2H, m), 2.58 (2H, m); 13C NMR (100.6 MHz, CDCl3) dC: 156.7,
135.0, 132.6, 121.1, 119.9, 116.3, 31.3 (t, JC–F¼22.1 Hz), 28.4; 19F NMR
(376.3 MHz, CDCl3) dF: ꢀ81.5, ꢀ114.5, ꢀ124.7, ꢀ126.4; HRMS (EI) m/
z calcd (Mþ) for C12H9F9OS2 403.9951, found 403.9948.
1H NMR (400 MHz, CDCl3) dH: 8.19 (2H, d, J¼8.8 Hz), 7.67 (2H, d,
J¼8.8 Hz), 2.76 (2H, t, J¼7.4 Hz), 1.65 (2H, quint, J¼7.4 Hz), 1.40 (2H,
quint, J¼7.4 Hz), 1.28 (4H, m), 0.89 (3H, t, J¼7.0 Hz); 13C NMR
(100.6 MHz, CDCl3) dC: 147.3,146.1,125.8, 124.0, 39.1, 31.3, 28.9, 28.1,
22.4, 13.9; HRMS (EI) m/z calcd (Mþ) for C12H17NO2S2 271.0701,
found 271.0693.
3.6.16. Entry 16: 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-
1-decyl 2-pyridyl disulfide38. Yield 0.955 g, 60%, as a colourless solid;
mp (trifluoroethanol) 33–35 ꢁC; IR (CH2Cl2): nmax 1242 (C–F), 499
(S–S) cmꢀ1; 1H NMR (400 MHz, CDCl3) dH: 8.51 (1H, m) 7.65 (2H, m),
7.14 (1H, m), 3.04 (2H, m), 2.60 (2H, m); 13C NMR (100.6 MHz, CDCl3)
dC:158.9,150.0,137.0,121.2,120.2, 31.6(t,JC–F¼22.0 Hz), 29.3; 19FNMR
(376.3 MHz, CDCl3) dF: ꢀ81.2, ꢀ114.1, ꢀ122.1, ꢀ122.3, ꢀ122.3, ꢀ123.1,
ꢀ123.8, ꢀ126.5; HRMS (ESI) m/z calcd (MþþH) for C15H9F17NS2
589.9905, found 589.9982, Found: C 30.61%, H 1.36%, N 2.40%, S
10.99%; C15H9F17NS2 requires C 30.57%, H 1.37%, N 2.38%, S 10.88%.
3.6.9. Entry 9: 2-hydroxyethyl p-nitrophenyl disulfide. Yield 0.474 g,
76%, as pale-yellow oil; IR (neat): nmax 3359 (OH), 1513, 1340 (NO2),
469 (S–S) cmꢀ1
;
1H NMR (300 MHz, CDCl3) dH: 8.14 (2H, d,
J¼9.0 Hz), 7.66 (2H, d, J¼9.0 Hz), 3.85 (2H, t, J¼5.9 Hz), 2.93 (2H, t,
J¼5.9 Hz), 2.59 (1H, br s); 13C NMR (75.5 MHz, CDCl3) dC: 146.5,
146.2, 125.9, 124.0, 60.0, 41.3; HRMS (EI) m/z calcd (Mþ) for
C8H9NO3S2 231.0024, found 231.0018; CHN Found: C 41.48%, H
3.90%, N 6.02, S 27.80%; C8H9NO3S2 requires C 41.55%, H 3.92%, N
6.06%, S 27.72%.
3.6.10. Entry 10: 1-butyl 2-pyridyl disulfide36. Yield 0.468 g, 87%, as
3.6.17. Entry 17: 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-
1-decyl p-nitrophenyl disulfide. Yield 1.060 g, 62%, as a yellow solid;
pale-yellow oil; IR (CHCl3): nmax 478 (S–S) cmꢀ1
;
1H NMR
(400 MHz, CDCl3) dH: 8.45 (1H, m), 7.73 (1H, m), 7.63 (1H, m), 7.06
(1H, m), 2.80 (2H, t, J¼7.4 Hz), 1.68 (2H, quint, J¼7.4 Hz), 1.42 (2H,
IR (CH2Cl2): nmax 1520, 1342 (NO2), 469 (S–S) cmꢀ1 1H NMR
;
(400 MHz, CDCl3) dH: 8.22 (2H, d, J¼9.0 Hz), 7.70 (2H, d, J¼9.0 Hz),
sext, J¼7.4 Hz), 0.90 (3H, t, J¼7.4 Hz), 13C NMR (75.5 MHz, CDCl3) dC
:
2.98 (2H, m), 2.53 (2H, m, H-20); 13C NMR (100.6 MHz, CDCl3) dC
:
160.7, 149.5, 136.8, 120.4, 119.5, 38.7, 30.9, 21.6, 13.5; HRMS (EI) m/z
146.7, 145.3, 126.4, 124.3, 31.5 (t, JC–F¼22.0 Hz), 29.2; 19F NMR
(376.3 MHz, CDCl3) dF: ꢀ81.2, ꢀ114.0, ꢀ122.0, ꢀ122.2, ꢀ122.2,
ꢀ123.1, ꢀ123.6, ꢀ126.4; HRMS (ESI) m/z calcd (MþþH) for
C16H9F17NO2S2 633.9803, found 633.9801.
calcd (Mþ) for C9H13NS2 199.0489, found 199.0493.
3.6.11. Entry 11: 2-benzoxazolyl 1-propyl disulfide. Yield 0.560 g,
92%, as a colourless semi-solid; IR (CH2Cl2): nmax 469 (S–S) cmꢀ1; 1H
NMR (300 MHz, CDCl3) dH: 7.67 (1H, m), 7.48 (1H, m), 7.30 (2H, m),
2.97 (2H, t, J¼7.2 Hz), 1.80 (2H, sext, J¼7.2 Hz), 1.02 (3H, t, J¼7.2 Hz);
13C NMR (75.5 MHz, CDCl3) dC: 163.6, 152.4, 142.0, 124.7, 124.5,
3.6.18. Entry 18: 2-benzoxazolyl 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-
Heptadecafluoro-1-decyl disulfide. Yield 0.935 g, 55%, as a colourless
solid; IR (CH2Cl2): nmax 1241 (C–F), 500 (S–S) cmꢀ1 1H NMR
;