D.P. Halbach, C.G. Hamaker / Journal of Organometallic Chemistry 691 (2006) 3349–3361
3357
(found) for C30H30ClBrF6NPRuS: C, 45.15 (44.97); H, 3.79
(3.72); N, 1.76 (1.77)%. Epa = 1255 mV.
4.5.6. [RuCl(g6-p-cymene)(PhCH2S-C6H4-2-CH@N-
C6H4-3-CF3)][PF6] ([4f][PF6])
1
Orange solid, 47% yield. H NMR (d, ppm, CDCl3):
8.54 (s, 1H, CH@N), 8.21 (br s, 1H, Har), 8.00 (m, 2H,
Har), 7.72 (m, 3H, Har), 7.38 (td, J = 7.6 Hz, 1.2 Hz, 1H,
Har), 7.23 (t, J = 7.6 Hz, 1H, Har), 7.15 (t, J = 7.6 Hz,
2H, Har), 7.09 (d, J = 7.6 Hz, 1H, Har), 6.75 (d,
J = 7.2 Hz, 2H, Har), 5.60 (d, J = 6.0 Hz, 1H, Hcymene),
5.48 (d, J = 6.4 Hz, 1H, Hcymene), 5.39 (d, J = 6.4 Hz,
1H, Hcymene), 5.34 (d, J = 6.0 Hz, 1H, Hcymene), 4.60 (d,
J = 12.8 Hz, 1H, SCH2), 3.44 (br d, J = 12.8 Hz, 1H,
SCH2), 2.56 (ꢁsept, J = 7.2 Hz, 1H, CH(Me)2), 1.74 (s,
3H, CH3-cymene), 1.02 (d, J = 7.2 Hz, 3H, CH(CH3)2),
0.81 (d, J = 7.2 Hz, 3H, CH(CH3)2). IR (cmꢀ1, Nujol):
1609 (C@N). Anal. Calc. (found) for C31H30ClF9NPRuS:
C, 47.30 (47.09); H, 3.84 (3.84); N, 1.78 (1.81)%.
Epa = 1270 mV.
4.5.3. [RuCl(g6-p-cymene)(PhCH2S-C6H4-2-CH@N-
C6H4-4-OPh)][PF6] ([4c][PF6])
Tan solid, 48% yield. 1H NMR (d, ppm, CDCl3): 8.56 (s,
1H, CH@N), 7.97 (d, J = 7.6 Hz, 1H, Har), 7.82 (d,
J = 8.8 Hz, 2H, Har), 7.71 (td, J = 8.4 Hz, 0.8 Hz, 1H,
Har), 7.38 (m, 3H, Har), 7.24–7.04 (m, 9H, Har), 6.76 (d,
J = 8.8 Hz, 2H, Har), 5.56 (d, J = 6.4 Hz, 1H, Hcymene),
5.47 (d, J = 6.0 Hz, 1H, Hcymene), 5.42 (d, J = 6.0 Hz,
1H, Hcymene), 5.39 (d, J = 6.4 Hz, 1H, Hcymene), 4.59 (d,
J = 13.2 Hz, 1H, SCH2), 3.40 (br d, J = 13.2 Hz, 1H, d,
1H, SCH2), 2.61 (ꢁsept, J = 6.8 Hz, 1H, CH(Me)2), 1.75
(s, 3H, CH3-cymene), 1.08 (d, J = 7.2 Hz, 3H, CH(CH3)2),
0.94 (d, J = 6.8 Hz, 3H, CH(CH3)2). IR (cmꢀ1, Nujol):
1609 (C@N). Anal. Calc. (found) for C36H35ClF6NOPRuS:
C, 53.30 (53.60); H, 4.35 (4.28); N, 1.73 (1.82)%.
Epa = 1218 mV.
4.5.7. [RuCl(g6-p-cymene)(PhCH2S-C6H4-2-CH@N-
C6H4-3-I)][PF6] ([4g][PF6])
1
4.5.4. [RuCl(g6-p-cymene)(PhCH2S-C6H4-2-CH@N-
C6H4-4-iPr)][PF6] ([4d][PF6])
Orange solid, 61% yield. H NMR (d, ppm, CDCl3):
8.50 (s, 1H, CH@N), 8.26 (br s, 1H, Har), 7.90 (d,
J = 7.6 Hz, 1H, Har), 7.75 (m, 3H, Har), 7.37 (t,
J = 7.6 Hz, 1H, Har), 7.31 (t, J = 8.0 Hz, 1H, Har), 7.23
(t, J = 7.6 Hz, 1H, Har), 7.15 (t, J = 7.6 Hz, 2H, Har),
7.07 (d, J = 7.6 Hz, 1H, Har), 6.74 (d, J = 7.2 Hz, 2H,
Har), 5.57 (d, J = 6.0 Hz, 1H, Hcymene), 5.48 (d,
J = 6.4 Hz, 1H, Hcymene), 5.38 (appearent d, J = 6.0 Hz,
2H, Hcymene), 4.61 (d, J = 13.2 Hz, 1H, SCH2), 3.40 (br
d, J = 13.2 Hz, 1H, SCH2), 2.57 (ꢁsept, J = 7.0 Hz, 1H,
CH(Me)2), 1.77 (s, 3H, CH3-cymene), 1.06 (d, J = 7.2 Hz,
3H, CH(CH3)2), 0.89 (d, J = 6.8 Hz, 3H, CH(CH3)2). IR
(cmꢀ1, Nujol): 1603 (C@N). Anal. Calc. (found) for
C30H30ClF6NPIRuS: C, 42.64 (42.37); H, 3.58 (3.51); N,
1.66 (1.65)%. Epa = 1263 mV.
1
Orange solid, 53% yield. H NMR (d, ppm, CDCl3):
8.54 (s, 1H, CH@N), 7.95 (d, J = 7.6 Hz, 1H, Har), 7.74
(d, J = 8.0 Hz, 2H, Har), 7.70 (t, J = 7.6 Hz, 1H, Har),
7.35 (m, 3H, Har), 7.22 (t, J = 7.6 Hz, 1H, Har), 7.14 (t,
J = 7.6 Hz, 2H, Har), 7.08 (d, J = 7.2 Hz, 1H, Har), 6.74
(d, J = 7.6 Hz, 2H, Har), 5.53 (d, J = 6.0 Hz, 1H, Hcymene),
5.45 (d, J = 6.0 Hz, 1H, Hcymene), 5.39 (d, J = 6.0 Hz, 1H,
H
cymene), 5.36 (d, J = 6.0 Hz, 1H, Hcymene), 4.60 (d,
J = 13.2 Hz, 1H, SCH2), 3.43 (br d, J = 13.2 Hz, 1H,
SCH2), 2.98 (ꢁsept, J = 6.8 Hz, 1H, CH(Me)2-SN), 2.55
(ꢁsept, J = 6.8 Hz, 1H, CH(Me)2-cymene), 1.73 (s, 3H,
CH3-cymene), 1.29 + 1.28 (d, J = 7.2 Hz + d, J = 6.8 Hz,
6H total, CH(CH3)2-SN), 1.03 (d, J = 6.8 Hz, 3H, CH-
(CH3)2-cymene), 0.79 (d, J = 6.8 Hz, 3H, CH(CH3)2-cymene).
IR (cmꢀ1, Nujol): 1607 (C@N). Anal. Calc. (found) for
C33H37ClF6NPRuS: C, 52.07 (51.86); H, 4.90 (4.82); N,
1.84 (1.94)%. Epa = 1209 mV.
4.5.8. [RuCl(g6-p-cymene)(PhCH2S-C6H4-2-CH@N-
C6H4-3-OMe)][PF6] ([4h][PF6])
1
Orange solid, 71% yield. H NMR (d, ppm, CDCl3):
8.53 (s, 1H, CH@N), 7.93 (d, J = 7.6 Hz, 1H, Har),
7.69 (t, J = 7.6 Hz, 1H, Har), 7.45 (s, 1H, Har), 7.39
(m, 4H, Har), 7.22 (m, 1H, Har), 7.04 (m, 3H, Har),
6.95 (m, 1H, Har), 6.76 (d, J = 7.2 Hz, 2H, Har), 5.51
(d, J = 6.0 Hz, 1H, Hcymene), 5.45 (d, J = 6.4 Hz, 1H,
4.5.5. [RuCl(g6-p-cymene)(PhCH2S-C6H4-2-CH@N-
C6H4-4-Me)][PF6] ([4e][PF6])
1
Orange solid, 52% yield. H NMR (d, ppm, CDCl3):
8.51 (s, 1H, CH@N), 7.94 (d, J = 7.6 Hz, 1H, Har), 7.70
(m, 3H, Har), 7.36 (t, J = 7.6 Hz, 1H, Har), 7.31 (d,
J = 8.0 Hz, 2H, Har), 7.22 (t, J = 7.2 Hz, 1H, Har), 7.14
(t, J = 7.2 Hz, 2H, Har), 7.09 (d, J = 7.2 Hz, 1H, Har),
6.75 (d, J = 7.2 Hz, 2H, Har), 5.52 (d, J = 6.0 Hz, 1H,
H
cymene), 5.38 (m, 2H, Hcymene), 4.60 (d, J = 12.8 Hz,
1H, SCH2), 3.92 (s, 3H, OCH3), 3.44 (br d,
J = 12.8 Hz, 1H, SCH2), 2.57 (ꢁsept, J = 6.8 Hz, 1H,
CH(Me)2), 1.75 (s, 3H, CH3-cymene), 1.04 (d, J = 7.2 Hz,
3H, CH(CH3)2), 0.87 (d, J = 6.4 Hz, 3H, CH(CH3)2).
IR (cmꢀ1, Nujol): 1596 (C@N). Anal. Calc. (found) for
C31H33ClF6NOPRuS: C, 49.70 (50.06); H, 4.44 (4.42);
N, 1.87 (1.93)%. Epa = 1235 mV.
H
cymene), 5.45 (d, J = 6.0 Hz, 1H, Hcymene), 5.40 (d,
J = 6.4 Hz, 1H, Hcymene), 5.35 (d, J = 6.4 Hz, 1H, Hcymene),
4.59 (d, J = 13.2 Hz, 1H, SCH2), 3.44 (br d, J = 13.2 Hz,
1H, SCH2), 2.56 (ꢁsept, J = 6.8 Hz, 1H, CH(Me)2), 2.42
(s, 3H, CH3-SN), 1.75 (s, 3H, CH3-cymene), 1.03 (d,
J = 6.8 Hz, 3H, CH(CH3)2), 0.89 (d, J = 6.8 Hz, 3H,
CH(CH3)2). IR (cmꢀ1, Nujol): 1607 (C@N). Anal. Calc.
(found) for C31H33ClF6NPRuS: C, 50.78 (50.64); H, 4.54
(4.50); N, 1.91 (2.10)%. Epa = 1205 mV.
4.5.9. [RuCl(g6-p-cymene)(PhCH2S-C6H4-2-CH@N-
C6H5)][PF6] ([4i][PF6])
1
Orange solid, 65% yield. H NMR (d, ppm, CDCl3):
8.50 (s, 1H, CH@N), 7.90 (d, J = 7.6 Hz, 1H, Har), 7.76