5
02
H. Firouzabadi, B. Karimi
PAPER
Table 3 Comparison of Deoxygenation Reaction in the Literature with WCl -NaI and WCl -Zn Methods
6
6
(CH ) SiI22 (PipH) WS4
24
NaBH -CoCl2
h (yield %)
30
Sm-NiCl -KI
h (yield %)
25
NaI-Organic acids2g
h (yield %)
Substrate
WCl -NaI WCl -Zn
h (yield %) h (yield %) h (yield %) h (yield %)
6
6
3 3
2
4
2
PhSOPh
0.58 (95)
0.17 (92)
0.33 (95)
0.17 (96)
0.08 (85)
0.17 (84)
0.17 (82)
0.3 (89)
0.75 (88)
0.7 (89)
0.5 (92)
0.33 (95)
0.7 (91)
Ð
no reaction
no reaction
no reaction
no reaction
2 (78)
2 (69)
2 (53)
Ð
Ð
Ð
Ð
Ð
Ð
4 (76)
5 (67)
PhCH SOCH Ph
Ð (10)
2
2
PhSOCH Ph
PhSOCH CH=CH 0.17 (80)
Ð
Ð
Ð
Ð
Ð
Ð
Ð
Ð
Ð
Ð
Ð
Ð
2
Ð
2
2
PhSO Cl
16 (97)
17 (94)
14 (85)
12 (95)
16 (100)
16 (89)
16 (86)
Ð
3 (70)
3 (62)
3 (68)
Ð
2
p-MeC H SO Cl
6
4
2
p-BrC H SO Cl
6
4
2
PhSO Na
2
(
25 mL). The organic layer was separated and dried (Na SO ). Re-
(4) Cintas, P. Activated Metals in Organic Synthesis; CRC: Boca
Raton, 1993.
(5) Fujiwara, Y.; Ishikawa, R.; Akiyama, F.; Teramishi, S. J. Org.
2
4
moval of the solvent gave almost pure product. Further purification
was achieved by recrystallization from petroleum ether which af-
forded dibenzyl sulfide 2j (0.18 g, 85%), mp 47Ð48¡C (lit.2g mp
Chem. 1978, 43, 2477.
4
8¡C).
(6) Sharpless, K. B.; Umbreit, M. A.; Nieh, M. T.; Flood,T. C.
J. Am. Chem. Soc. 1972, 94, 6538.
Reductive Coupling of Sulfonyl Chlorides with WCl ÐZn; Typ-
ical Procedure
In a round-bottomed flask (25 mL) equipped with a condenser and
(7) McMurry, J. E.; Fleming, M. P. J. Org. Chem. 1975, 40, 2555.
(8) Drabowicz, J.; Mikolajczyk, M. Synthesis 1976, 527.
(9) Drabowicz, J.; Mikolajczyk, M. Synthesis 1978, 138.
(10) Baliki, R. Synthesis 1991, 155.
(11) Akita, Y.; Inaba, M.; Uchida, H.; Ohta, A. Synthesis 1977,
792.
6
a magnetic stirrer, WCl (0.48g, 1.2 mmol) was added to a suspen-
6
sion of benzenesulfonyl chloride (0.18g, 1 mmol) and Zn powder
(
0.19 g, 3 mmol) in anhyd MeCN (10 mL) and the resulting mixture
was stirred under reflux condition. After completion of the reaction
20 min) aq NaOH (10%, 25 ml) was added and the mixture was ex-
(12) Nuzzo, R. G.; Simon, H. G.; Sanfilippo, J. J. Org. Chem.
(
1977, 42, 568.
tracted according to the preceding procedure. Further purification
was achieved by recrystallization of the compound from petroleum
ether to give diphenyl disulfide (0.10g, 89%), mp 58Ð59¡C, (lit.25
mp 58Ð60¡C).
(13) Olah, G. A.; Surya Prakash, G. K.; Ho, T. L. Synthesis 1976,
810.
(14) Ho, T. L.; Wong, C. M. Synthesis 1973, 206.
(15) Karchmer, J. H. The Analytical Chemistry of Sulfur and its
Compounds; Wiley: New York, 1972; p 103.
(
16) Parry, R. J. Tetrahedron 1983, 39, 1215.
Acknowledgement
(17) Oae, S.; Togo, H. Synthesis 1982, 152.
(
18) Adams, R.; Marvel, C. S. ÓOrganic SynthesesÓ; Wiley: New
York, 1956; Coll. Vol. 1, pp504Ð506.
19) Sheppard, W. A. ÓOrganic SynthesesÓ; Wiley: New York,
We are thankful to the Shiraz University Research Council for sup-
port of this work.
(
1
973; Coll. Vol. 5, pp 843Ð845.
(
(
20) Kulka, M. J. Am. Chem. Soc. 1950, 72, 1215.
21) G. A.; Narang,, S. C.; Field, L. D.; Karpeles, R. J. Org. Chem.
1981, 46, 2408.
References
(1) Soladie, G. Synthesis 1981, 185.
Carreno, M. C. Chem. Rev. 1995, 95, 1717.
(22) G. A.; Narang,, S. C.; Field, L. D.; Salem, G. F. J. Org. Chem.
Davies, S. G.; Loveridge, T.; Clough, J. M. Synlett 1997, 66.
2) For reviews, see: Madesclaire, M. Tetrahedron 1988, 44,
1980, 45, 4792.
(
(23) Kiellbasinski, P.; Drabowicz, J.; Mikolajczyk, M. J. Org.
Chem. 1982, 47, 4806.
(24) Dhar, P.; Ranjan, R.; Chandrasekaran, S. J. Org. Chem. 1990,
55, 3728.
(25) Zhan, Z.; Guo, H.; zhan, Y. Synth. Commun. 1997, 27, 2749.
(26) Suzuki, H.; Nakamura, T.; Yoshikawa, M. J. Chem. Res., (S)
1994, 2, 70.
(27) Kagabu, S. Org. Prep. Proced. Int. 1989, 21, 388.
(28) Firouzabadi, H.; Shiriny, F. Tetrahedron 1996, 52, 14929.
Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1998, 739.
Firouzabadi, H.; Iranpoor, N.; Karimi, B. J. Chem. Res., (S)
1998, 664.
(29) Sobota, P.; Pluzinski, T. Tetrahedron 1981, 37, 942.
(30) Chasar, D. W. J. Org. Chem. 1971, 36, 613.
(31) BeilsteinÕs Handbuch der Organischem Chemie,Springer
Verlag: Berlin, 1923 a) 6, I, 663. b) 6, III, 982. c) 6, II, 453. d)
6, IV, 1479.
6
537.
Drabowicz, J.; Numata, T.; Oae, S. Org. Prep. Proced. Int.
977, 9, 63.
For recent leading references, see:
a) Drabowicz, J.; Dudzinski, B.; Mikolajczyk, M. Synlett
992, 252.
b) Mohanazadeh, F.; Momeni, A. R.; Ranjbar, Y. Tetra-
hedron Lett. 1994, 35, 6127 and references cited therein.
c) Lee, G. H.; Choi, E. B.; Lee, E.; Pak, C. S. ibid. 1994, 35,
195.
d) Zhang, Y.;Yu, Y.; Bao, W. Synth. Commun. 1995, 25,
825.
1
(
1
(
(
2
(
1
(e)Wang, J. Q.; Zhang, Y. M. ibid. 1995, 25 3545.
(f)Nicolas, E.; Vilaseca, M.; Giralt, E. Tetrahedron 1995, 51,
5
(
1
(
701.
g) Fujiki, K.; Kurita, S.; Yoshida, E. Synth. Commun. 1996,
9, 3619.
h) Wang, Y.; Koreeda, M. Synlett 1996, 885.
(32) Kornblum, N.; Cheng, L.; Kerber, R. C.; Kestner, M.M.
J. Org. Chem. 1976, 41, 1560
(33) Aldrich Catalog, Handbook of Fine Chemicals 1990Ð91.
nd
(
3) House, H. O. Modern Synthetic Reactions, 2 Ed.; Benjamin
Cummings: California, 1972, pp 15, 16, 215Ð216.
Synthesis 1999, No. 3, 500Ð502 ISSN 0039-7881 © Thieme Stuttgart · New York