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M. Kirihara et al.
SHORT PAPER
due was purified by silica gel column chromatography (hexane–
EtOAc) to afford the pure products.
1H NMR (CDCl3): d = 3.69 (4 H, s), 6.22 (2 H, d, J = 3.17 Hz), 6.33
(2 H, dd, J = 1.95, 2.44 Hz), 7.39 (2 H, dd, J = 0.73, 1.95 Hz).
13C NMR (CDCl3): d = 35.7, 108.9, 110.7, 142.4, 150.2.
Oxidation of L-Cysteine to L-Cystine
To a stirred solution of L-cysteine (606 mg, 5 mmol) in H2O (10
mL) was added NaI (7.5 mg, 0.05 mmol) and 30% H2O2 (0.55 mL,
5 mmol) and the mixture was stirred at r.t. for 0.5 h. The precipitated
L-cystine was collected by filtration. The desired L-cystine was ob-
tained as a colorless solid (574 mg, 96%). The NMR data for this
compound were identical with those in the literature8 and with an
authentic sample purchased from Kishida Reagents Chemicals; mp
216–220 °C (dec.) [Lit.9 mp 260–261 °C (dec.)].
p-Ditolyl Disulfide
Oxidation of p-tolylthiol (0.124 g, 1.0 mmol) following the general
procedure gave p-ditolyl disulfide (0.121 g, 99%) as colorless crys-
tals; mp 44–45 °C (Lit.10 mp 43–44 °C).
1H NMR (CDCl3): d = 2.31 (6 H, s), 7.10 (4 H, d, J = 8.05 Hz), 7.38
(4 H, d, J = 8.05 Hz).
13C NMR (CDCl3): d = 21.0, 128.6, 129.8, 133.9, 137.4.
1H NMR (D2O): d = 3.10 (2 H, dd, J = 8.17, 14.76 Hz), 3.30 (2 H,
dd, J = 3.96, 14.76 Hz), 4.03 (2 H, dd, J = 3.96, 8.17 Hz).
Bis(4-chlorophenyl) Disulfide
Oxidation of 4-chlorophenylthiol (0.144 g, 1.0 mmol) following the
general procedure gave bis(4-chlorophenyl) disulfide (0.132 g,
92%) as colorless crystals; mp 72–73 °C (Lit.10 mp 71–72 °C).
1H NMR (CDCl3): d = 7.27 (4 H, d, J = 8.54 Hz), 7.40 (4 H, d,
J = 8.54 Hz).
Dibenzyl Disulfide
Oxidation of benzyl-1-thiol (0.124 g, 1.0 mmol) following the gen-
eral procedure gave dibenzyl disulfide (0.118 g, 96%) as colorless
crystals; mp 70–71 °C (Lit.10 mp 70–71 °C).
1H NMR (CDCl3): d = 3.60 (4 H, s), 7.22–7.35 (10 H, m).
13C NMR (CDCl3): d = 43.3, 127.4, 128.5, 129.4, 137.4.
13C NMR (CDCl3): d = 129.3, 129.4, 133.7, 135.1.
Bis(4-nitrophenyl) Disulfide
Oxidation of 4-nitrophenylthiol (0.155 g, 1.0 mmol) following the
general procedure gave bis(4-nitrophenyl) disulfide (0.136 g, 93%)
as brown crystals; mp 188–189 °C (Lit.12 mp 182 °C).
1H NMR (CDCl3): d = 7.62 (4 H, d, J = 9.02 Hz), 8.20 (4 H, d,
J = 9.02 Hz).
Dibutyl Disulfide
Oxidation of butyl-1-thiol (0.090 g, 1.0 mmol) following the gener-
al procedure gave dibutyl disulfide (0.089 g, 96%) as a colorless oil.
The NMR data of this compound were identical with those in the lit-
erature.1e
1H NMR (CDCl3): d = 0.93 (6 H, t, J = 7.35 Hz), 1.42 (4 H, sext,
J = 7.35 Hz), 1.66 (4 H, quint, J = 7.35 Hz), 2.69 (4 H, t, J = 7.35
Hz).
13C NMR (CDCl3): d = 124.0, 124.4, 126.4, 144.1.
Acknowledgment
13C NMR (CDCl3): d = 13.7, 21.6, 31.3, 38.9.
This work was carried out with financial support from the Forum on
Iodine Utilization.
Didodecyl Disulfide
Oxidation of dodecyl-1-thiol (0.202 g, 1.0 mmol) following the
general procedure gave didodecyl disulfide (0.201 g, 97%) as col-
orless crystals; mp 32 °C (Lit.4 mp 32 °C).
1H NMR (CDCl3): d = 0.88 (6 H, t, J = 6.59 Hz), 1.23–1.40 (36 H,
m), 1.67 (4 H, quint, J = 7.38 Hz), 2.68 (4 H, t, J = 7.38 Hz).
13C NMR (CDCl3): d = 14.1, 22.7, 28.5, 29.2, 29.3, 29.5, 29.6, 29.6,
30.1, 31.9, 39.2.
References
(1) (a) Uemura, S. In Comprehensive Organic Synthesis, Vol. 7;
Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford,
1991, 757. (b) Aida, T.; Akasaka, T.; Furukawa, N.; Oae, S.
Bull. Chem. Soc. Jpn. 1976, 49, 1441. (c) Wu, X.; Reike, R.
D.; Zhu, L. Synth. Commun. 1996, 26, 191. (d) Drabowicz,
J.; Mikolajczyk, M. Synthesis 1980, 32. (e) Noureldine, N.
A.; Caldwell, M.; Hendry, J.; Lee, D. G. Synthesis 1998,
1587. (f) Tam, J. P.; Wu, C.-R.; Liu, W.; Zhang, J.-W. J. Am.
Chem. Soc. 1991, 113, 6657. (g) Sanz, R.; Aguado, R.;
Pedrosa, M. R.; Arnáiz, F. J. Synthesis 2002, 856.
(h) Karimi, B.; Hazarkhani, H.; Zareyee, D. Synthesis 2002,
2513.
Dicyclohexyl Disulfide
Oxidation of cyclohexylthiol (0.116 g, 1.0 mmol) following the
general procedure gave dicyclohexyl disulfide (0.113 g, 97%) as a
colorless oil. The NMR data of this compound were identical with
those in the literature.11
1H NMR (CDCl3): d = 1.20–1.37 (10 H, m), 1.60–1.63 (2 H, m),
1.77–1.79 (4 H, m), 2.03–2.00 (4 H, m), 2.65–2.72 (2 H, m).
(2) (a) Nagano, T.; Yoshikawa, K.; Hirobe, M. Tetrahedron
Lett. 1980, 21, 297. (b) Cervilla, A.; Corma, A.; Fornés, V.;
Llopis, E.; Palanca, P.; Rey, F.; Ribera, A. J. Am. Chem. Soc.
1994, 116, 1595. (c) Iranpoor, N.; Zeynizadeh, B. Synthesis
1999, 49. (d) Kirihara, M.; Okubo, K.; Uchiyama, T.; Kato,
Y.; Ochiai, Y.; Matsushita, S.; Hatano, A.; Kanamori, K.
Chem. Pharm. Bull. 2004, 52, 625. (e) Arisawa, M.; Sugata,
C.; Yamaguchi, M. Tetrahedron Lett. 2005, 46, 6907.
(3) (a) Price, C. C.; Stacy, G. W. Org. Synth. Coll. Vol. III;
Wiley: New York, 1955, 86. (b) Kesavan, V.; Bonnet-
Delpon, D.; Bégué, J.-P. Synthesis 2000, 223.
13C NMR (CDCl3): d = 25.7, 26.1, 30.9, 32.8, 50.0.
Di(tert-octyl) Disulfide
Oxidation of tert-octylthiol (0.146 g, 1.0 mmol) following the gen-
eral procedure gave di(tert-octyl) disulfide (0.35 g, 28%) as a color-
less oil. The NMR data of this compound were identical with an
authentic sample purchased from Tokyo Chemical Industry.
1H NMR (CDCl3): d = 1.03 (18 H, s), 1.38 (12 H, s), 1.66 (4 H, s).
13C NMR (CDCl3): d = 30.0, 31.8, 32.8, 51.5, 54.6.
(4) Wallace, T. J. J. Org. Chem. 1966, 31, 1217.
Difurfuryl Disulfide
(5) (a) Behzad, Z. J. Chem. Research, Synop. 2002, 564.
(b) Aida, T.; Akasaka, T.; Furukawa, N.; Oae, S. Bull. Chem.
Soc. Jpn. 1976, 49, 1441. (c) Drabowicz, J.; Mikoïajczyk,
M. Synthesis 1980, 32.
Oxidation of furfurylthiol (0.114 g, 1.0 mmol) following the general
procedure gave difurfuryl disulfide (0.113 g, 98%) as a colorless oil.
The NMR data of this compound were identical with those in the lit-
erature.11
Synthesis 2007, No. 21, 3286–3289 © Thieme Stuttgart · New York