Journal of Sulfur Chemistry
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CH2O, CHO), 3.68–3.88 (m, 6 H, PCH2CH2O), 7.16–7.28 (m, 30 H, Ph). 13C NMR (100.62
1
MHz, CDCl3): δ = 28.52 (PhCH2), 31.27 and 33.54 (2 d, JPC = 50.2 and 49.1 Hz, PCH2),
63.93 (d, 2JPC = 2.4 Hz, CH2O), 65.32 (d, 2JPC = 2.3 Hz, CH2O), 70.65 (CH2O), 77.82 (CHO),
126.45 (Cp in Ph), 128.18 (Co in Ph), 128.64 (Cm in Ph), 140.67 (d, 3JPC = 14.2 Hz, Ci in Ph).
31P NMR (161.98 MHz, CDCl3): δ = 49.00 (br s). IR (film, ν, cm−1): 753 (P − C), 600 (P = S).
Anal. Calcd for C57H71O3P3S3: C, 68.92; H, 7.20; P, 9.35; S, 9.68. Found: C, 68.78%; H, 7.15%;
P, 9.30%; S, 9.73%.
4.2.2. 2-(2,3-Bis{2-[bis(4-chlorophenethyl)phosphorothioyl]ethoxy}propoxy)ethyl-[bis(4-
chlorophenethyl)]phosphine sulfide (8b)
1
Colorless oil; yield: 0.338 g (94%). H NMR (400.13 MHz, CDCl3): δ = 1.72–2.08 (m, 18 H,
PCH2), 2.76–2.83 (m, 12 H, CH2Ar), 3.35–3.42 (m, 5 H, CH2O, CHO), 3.73–3.82 (m, 6 H,
PCH2CH2O), 7.00–7.16 (m, 24 H in Ar). 13C NMR (100.62 MHz, CDCl3): δ = 27.72 (CH2Ar),
30.79 and 33.30 (2 d,1JPC = 50.0 and 48.3 Hz, PCH2), 65.06 (d, 2JPC = 2.4 Hz, CH2O), 66.81
(d, 2JPC = 2.3 Hz, CH2O), 70.99 (CH2O), 78.97 (CHO), 128.56 (C-2,6 in Ar), 129.43 (C-3,5 in
Ar), 132.01 (C-4 in Ar), 138.87 (d, 3JPC = 14.2 Hz, C-1 in Ar). 31P NMR (161.98 MHz, CDCl3):
δ = 48.09 (br s). IR (film, ν, cm−1): 775 (P −C), 653 (P= S). Anal. Calcd for C57H65Cl6O3P3S3:
C, 57.05; H, 5.46; Cl, 17.73; P, 7.74; S, 8.02. Found: C, 57.42%; H, 5.12%; Cl, 17.53%; P, 7.82%;
S, 8.13%.
4.2.3. 2-(3-[2-(Diphenethylphosphorothioyl)ethoxy]-2-[2-(diphenethylphosphorothioyl)-
ethoxy]methyl-2-methylpropoxy)ethyl(diphenethyl)phosphine sulfide (9a)
Colorless oil; yield: 0.276 g (90%). 1H NMR (400.13 MHz, CDCl3): δ = 0.82 (s, 3 H,
3
Me), 2.03–2.09 (m, 6 H, PCH2CH2O), 2.17–2.24 (m, 12 H, PCH2), 2.96 (dt, JPH = 9.8,
3
3
3JHH = 7.2 Hz, 12 H, PhCH2), 3.16 (s, 6 H, CH2O), 3.62 (dt, JPH = 18.4, JHH = 5.9 Hz,
6 H, PCH2CH2O), 7.20–7.29 (m, 30 H, Ph). 13C NMR (100.62 MHz, CDCl3): δ = 17.85 (Me),
1
28.66 (PhCH2), 31.69 and 33.83 (2 d, JPC = 49.9 and 48.3 Hz, PCH2), 40.58 (C), 65.50 (d,
2JPC = 2.8 Hz, CH2O), 73.89 (CCH2O), 126.59 (Cp in Ph), 128.31 (Co in Ph), 128.78 (Cm in
Ph), 140.76 (d, 3JPC = 14.4 Hz, Ci in Ph). 31P NMR (161.98 MHz, CDCl3): δ = 48.40. IR (film,
ν, cm−1): 758 (P − C), 599 (P =S). Anal. Calcd for C59H75O3P3S3: C, 69.38; H, 7.40; P, 9.10;
S, 9.42. Found: C, 69.40%; H, 7.72%; P, 9.29%; S, 9.58%.
4.2.4. 2-(2,2-Bis[2-(diphenethylphosphorothioyl)ethoxy]methylbutoxy)ethyl-
(diphenethyl)phosphine sulfide (9b)
Colorless oil; yield: 0.264 g (85%). 1H NMR (400.13 MHz, CDCl3): δ = 0.71 (t, 3J = 7.4 Hz,
3 H, Me), 1.22 (q, 3JHH = 7.4 Hz, 2 H, CH2Me), 2.02–2.07 (m, 6 H, PCH2CH2O), 2.15–2.22
3
3
(m, 12 H, PCH2), 2.93 (dt, JPH = 9.5, JHH = 7.2 Hz, 12 H, PhCH2), 3.14 (s, 6 H, CH2O),
3
3
3.62 (dt, JPH = 18.4, JHH = 6.0 Hz, 6 H, PCH2CH2O), 7.18–7.31 (m, 30 H, Ph). 13C NMR
(100.62 MHz, CDCl3): δ = 7.59 (Me), 23.01 (CH2Me), 28.64 (PhCH2), 31.40 and 33.54 (2 d,
1JPC = 50.3 and 48.3 Hz, PCH2), 42.93 (C), 65.44 (d, 2JPC = 3.6 Hz, CH2O), 71.49 (CCH2O),
126.57 (Cp in Ph), 128.28 (Co in Ph), 128.75 (Cm in Ph), 140.875 (d, 3JPC = 14.4 Hz, Ci in Ph).
31P NMR (161.98 MHz, CDCl3): δ = 48.47. IR (film, ν, cm−1): 753 (P− C), 600 (P= S). Anal.
Calcd for C60H77O3P3S3: C, 69.60; H, 7.50; P, 8.97; S, 9.29. Found: C, 69.40%; H, 7.72%; P,
8.59%; S, 9.14%.