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F. S. GOKSEL ET AL.
2,5-Diethoxy-3,6-di(octylthio)-1,4-benzoquinone (9c) and 2,5-Diethoxy-
3-octylthio-6-chloro-1,4-benzoquinone (10c). Compounds 9c and 10c were syn-
thesized by the reaction of 2,5-diethoxy-3,6-dichloro-1,4-benzoquinone (3; 0.148 g,
0.56 mmol) with octanethiol (4c; 0.09 mL, 1.12 mmol).
9c: Yield 0.035 g (13%); Brown oil; Rf = 0.45 (CHCl3-PET 1:1). IR (Film): 2962,
1560, 1662 cm−1. 1H NMR (499.74 MHz, CDCl3): δ = 0.79–0.82 (m, 6H, 2CH3), 1.17–1.51
(m, 24H, 12CH2; 6H, 2CH3CH2O–), 2.72–2.96 (m, 4H, 2S-CH2), 4.03–4.30 (m, 4H,
2CH3CH2O-). 13C NMR (125 MHz, CDCl3): δ = 13.0, 14.8, 21.6, 27.7, 28.1, 28.7, 30.8,
30.9, 34.4, 68.3, 127.6, 142.6, 178.1. MS (ESI, 70 eV): m/z (%) = 485.72 (M+). UV/Vis
(CHCl3): λmax = 243 nm. Anal. Calcd for C26H44O4S2: C, 64.42; H, 9.15. Found: C, 64.57;
H 10.26.
10c: Yield 0.122 g (58%); Red oil; Rf = 0.42 (CHCl3-PET 1:1). IR (Film): 2983,
1560, 1635, 1662 cm−1. 1H NMR (499.74 MHz, CDCl3): δ = 0.79–0.81 (t, J = 6.84, 3H,
CH3), 1.17–1.52 (m, 12H, 6CH2; 6H, 2CH3CH2O–), 2.93–2.96 (t, J = 7.32, 2H, S-CH2),
4.32–4.44 (m, 4H, 2CH3CH2O–). 13C NMR (125 MHz, CDCl3): δ = 13.0, 14.8, 14.9, 21.6,
27.6, 28.1, 28.1, 29.1, 30.8, 32.1, 69.5, 69.7, 122.8, 127.6, 153.8, 155.0, 174.1, 178.3. MS
(ESI, 70 eV): m/z (%) = 375.13 (M+). UV/Vis (CHCl3): λmax = 248, 295 nm. Anal. Calcd
for C18H27ClO4S: C, 57.66; H, 7.26. Found: C, 57.29; H, 7.20.
2,5-Diethoxy-3-heptylthio-6-chloro-1,4-benzoquinone(10d). Compound
10d was synthesized by the reaction of 2,5-diethoxy-3,6-dichloro-1,4-benzoquinone (3;
0.148 g, 0.56 mmol) with heptanethiol (4d; 0.08 mL, 0.56 mmol).
10d: Yield 0.127 g (49%); Red oil; Rf = 0.58 (CHCl3-PET 1:5). IR (Film): 2989,
1568, 1671 cm−1. 1H NMR (499.74 MHz, CDCl3): δ = 0.79–0.82 (m, 3H, 1CH3), 1.17–1.51
(m, 10H, 5CH2, 6H, 2CH3CH2O–), 2.93–2.97 (t, J = 7.32, 2H, S-CH2), 4.33–4.43 (m, 4H,
2CH3CH2O–). 13C NMR (125 MHz, CDCl3): δ = 13.0, 14.8, 14.9, 21.6, 27.6, 27.8, 29.1,
30.7, 32.1, 69.5, 69.7, 122.8, 127.6, 153.8, 155.0, 174.1, 178.3. MS (ESI, 70 eV): m/z (%)
= 360.17 (M+). UV/Vis (CHCl3): λmax = 244, 301 nm. Anal. Calcd for C17H25ClO4S: C,
56.58; H, 6.98. Found: C, 57.04; H, 7.28.
2,5-Diethoxy-3,6-di(pentylthio)-1,4-benzoquinone(9e). Compound 9e was
synthesized by the reaction of 2,5-diethoxy-3,6-dichloro-1,4-benzoquinone (3; 0.148 g,
0.56 mmol) with pentanethiol (4e; 0.06 mL, 0.56 mmol).
9e: Yield 0.16 g (72%); Red oil; Rf = 0.49 (CHCl3-PET 1:10). IR (Film): 2986,
1564, 1635, 1671 cm−1. 1H NMR (499.74 MHz, CDCl3): δ = 0.80–0.83 (t, J = 7.32, 6H,
2CH3), 1.33–1.52 (m, 12H, 6CH2; 6H, 2CH3CH2O–), 2.94–2.97 (t, J = 7.32, 4H, 2S-CH2),
4.32–4.44 (m, 4H, 2CH3CH2O-). 13C NMR (125 MHz, CDCl3): δ = 12.9, 14.9, 21.2, 28.8,
29.8, 32.1, 69.5, 127.5, 153.8, 178.3. MS (ESI, 70 eV): m/z (%) = 400.88 (M+). UV/Vis
(CHCl3): λmax = 244, 302 nm. Anal. Calcd for C20H32O4S2: C, 59.96; H, 8.05. Found: C,
60.38; H, 8.42.
2,5-Diethoxy-3,6-di(butylthio)-1,4-benzoquinone(9f). Compound 9f was
synthesized by the reaction of 2,5-diethoxy-3,6-dichloro-1,4-benzoquinone (3; 0.148 g,
0.56 mmol) with butanethiol (4f; 0.06 mL, 0.56 mmol).
9f: Yield 0.140 g (66%); Reddish-brown oil; Rf = 0.42 (CHCl3-PET 1:2). IR (Film):
2983, 1560, 1662 cm−1. 1H NMR (499.74 MHz, CDCl3): δ = 0.81–0.87 (m, 6H, 2CH3),
1.33–1.53 (m, 8H, 4CH2; 6H, 2CH3CH2O), 2.95–2.99 (t, J = 7.32, 4H, 2S-CH2), 4.27–4.46
(m, 4H, 2CH3CH2O–). 13C NMR (125 MHz, CDCl3): δ = 12.6, 14.8, 20.8, 31.2, 31.7,
69.1, 127.6, 155.8, 178.1. MS (ESI, 70 eV): m/z (%) = 373.74 (M+). UV/Vis (CHCl3):
λmax = 246 nm. Anal. Calcd for C18H28O4S2: C, 58.03; H, 7.58. Found: C 58.22; H, 7.95.