FULL PAPERS
H. Firouzabadi et al.
1
3
4
6
1
.6 (t, 1H), 2.8–3.1 (dd, 2H), 2.15 (s, 3H); C NMR (CDCl3,
3 MHz): d¼205.88, 141.51, 137.43, 133.28, 129.44, 129.22,
29.05, 128.18, 128.06, 49.89, 48.45, 30.71; IR: n¼1710 (C¼O)
[2] a) P. Anastas, J. C. Warner, Green Chemistry: Theory and
Practice, Oxford University Press: Oxford, 1998; b) P.
Tundo, P. Anastas, D. StC. Black, J. Breen, T. Collins,
S. Memoli, J. Miyamoto, M. Polyakoff, W. Tumas, Pure
Appl. Chem. 2000, 72, 1207.
ꢁ
1
þ
cm ; MS: m/e¼256 [M] ; anal. calcd. for C H OS: C 74.96,
1
6
16
H 6.29; found: C 75.2, H 6.28.
-Cyclohexylsulfanylbutan-2-one (4i): H NMR( CDCl ,
1
4
3
[
3] a) P. A. Grieco, Organic Synthesis in Water, Blacky Aca-
demic and Professional: London, 1998; b) C.-J. Li, T.-H.
Chan, Organic Reactions in Aqueous Media, John Wiley
2
2
50 MHz): d¼2.75–2.73 (ddþm, 5H), 2.17–2.18 (m, 2H),
13
.00 (m, 2H), 1.77 (m, 2H), 1.63 (m, 1H), 1.30 (m, 6H);
C
NMR (CDCl , 63 MHz): d¼207.25, 44.08, 34.34, 30.74, 26.10,
3
ꢁ
1
þ
4.10; IR: n¼1710 (C¼O) cm ; MS: m/e¼186 [M] ; anal.
&
Sons: New York, 1997; c) B. Cornils, W. A. Herrmann,
2
calcd. for C H OS: C 64.47, H 9.74; found: C 64.48, H 9.74.
Aqueous-Phase Organometallic Chemistry: Concepts and
Applications, Wiley-VCH: Weinheim, 1998.
10
18
1
3
-Cyclohexylsulfanylcyclohexanone (4j): H NMR (CDCl ,
3
2
3
1
4
50 MHz): d¼3.15 (m, 1H), 2.71–2.64 (m, 2H), 2.41–2.31 (m,
[4] a) D. C. Rideout, R. Breslow, J. Am. Chem. Soc. 1980,
H), 2.15–2.11 (m, 2H), 1.92 (m, 2H), 1.74–1.63 (m, 5H), 1.35–
1
1
02, 7816; b) R. Breslow, Acc. Chem. Res. 1991, 24,
59; c) J. B. F. N. Engberts, M. J. Blandamer, Chem.
1
3
.28 (m, 5H); C NMR (CDCl , 63 MHz): d¼209.11, 49.00,
3
2.36, 41.38, 34.51, 33.11, 26.28, 25.61; IR: n¼1700 (C¼O)
Commun. 2001, 1701.
ꢁ
1
þ
cm ; MS: m/e¼212 [M] ; anal. calcd. for C H OS: C 67.88,
1
2
20
[
5] a) J. H. Fendler, E. J. Fendler, Catalysis in Micellar and
Macromolecular Systems, Academic Press: London,
1975; b) Mixed Surfactant Systems, (Eds.: P. M. Holland,
D. N. Rubingh), American Chemical Society: Washing-
ton, DC, 1992; c) Structure and Reactivity in Aqueous
Solution, (Eds.: C. J. Cramer, D. G. Truhlar), American
Chemical Society: Washington, DC, 1994; d) Surfactant-
Enhanced Subsurface Remediation, (Eds.: D. A. Sabatini,
R. C. Knox, J. H., Harwell), American Chemical Society:
Washington, DC, 1994; e) K. Manabe, X. M. Sun, S. Ko-
bayashi, J. Am. Chem. Soc. 2001, 123, 10101.
H 9.49; found: C 67.25, H 9.48.
4
-[2-(3-Oxobutylsulfanyl)-ethylsulfanyl]-butan-2-one (4k):
1
H NMR (CDCl , 250 MHz): d¼2.76–2.70 (m, 12H), 2.18 (s,
3
13
6
3
H); C NMR (CDCl , 63 MHz): d¼207.00, 43.97, 32.63,
3
ꢁ
1
þ
0.45, 26.01; IR: n¼1710 (C¼O) cm ; MS: m/e ¼234 [M] ;
anal. calcd. for C H O S : C 51.25, H 7.74; found: C 51.19, H
10
18
2 2
7.72.
3
-[2-(3-Oxocyclohexylsulfanyl)-ethylsulfanyl]-cyclohex-
1
ane-1-one (4l) (Table 2, Entry 3): H NMR (CDCl , 250 MHz):
3
d¼3.20–3.10 (m, 2H), 2.76 (m, 4H), 2.7–2.65 (m, 2H), 2.42–
1
3
2.32 (m, 6H), 2.16–2.13 (m, 4H), 1.74–1.70 (m, 4H);
C
NMR (CDCl , 63 MHz): d¼208.53, 48.27, 42.68, 41.09, 31.74,
3
ꢁ
1
þ
[6] a) I. V. Berezin, K. Martinek, A. K. Yatsimirskii, Russ.
Chem. Rev. 1973, 42, 787; b) S. Tascioglu, Tetrahedron
3
0.91, 24.25; IR: n¼1700 (C¼O) cm ; MS: m/e ¼286 [M] ;
anal. calcd for C H O S : C 58.70, H 7.74; found: C 58.64, H
14
22
2 2
1
996, 52, 11113.
7.73.
4
-[3-(3-Oxobutylsulfanyl)-propylsulfanyl]-butan-2-one
[7] a) F. M. Menger, J. U. Rhee, H. K. Rhee, J. Org. Chem.
1975, 40, 3803; b) C. Larpent, E. Bernard, F. B. Menn,
H. Patin, J. Mol. Catal. A: Chem. 1997, 116, 277; c) T.
Dwars, U. Schmidt, C. Fischer, I. Grassert, R. Kempe,
R. Frçhlich, K. Drauz, G. Oehme, Angew. Chem., Int.
Ed. 1998, 37, 2851; d) I. Grassert, U. Schmidt, S. Ziegler,
C. Fischer, G. Oehme, Tetrahedron: Asymmetry 1998, 9,
1
(
4
4m): H NMR (CDCl , 250 MHz): d¼2.74 (m, 8H), 2.62 (m,
3
1
3
H), 2.18 (s, 6H), 2.18 (t, 2H); C NMR (CDCl , 63 MHz):
3
d¼207.13, 43.91, 31.33, 30.43, 29.34, 26.00; IR: n¼1710
ꢁ
1
þ
(
C¼O) cm ; MS: m/e ¼248 [M] ; anal. calcd. for C H O S :
1
1
20
2 2
C 53.19, H 8.12; found: C 53.15, H 8.11.
3
-[3-(3-Oxocyclohexylsulfanyl)-propylsulfanyl]-cyclohex-
1
ane-1-one (4n) (Table 2, Entry 4): H NMR (CDCl , 250 MHz):
3
4
193; e) R. Selke, J. Holz, A. Riepe, A. Borner, Chem.
d¼3.01–3.00 (m, 2H), 2.74–2.62 (tþm, 6H), 2.42–2.33 (m,
1
3
Eur. J. 1998, 4, 769; f) K. Yonehara, T. Hashizume, K.
Mori, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64,
5593; g) K. Yonehara, K. Ohe, S. Uemura, J. Org.
Chem. 1999, 64, 9381; h) M. S. Goedheijt, B. E. Hanson,
J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, J.
Am. Chem. Soc. 2000, 122, 1650.
6
(
2
H), 2.17–2.12 (m, 4H), 1.87–1.69 (m, 6H); C NMR
CDCl , 63 MHz): d¼209.10, 48.47, 43.24, 41.28, 31.93, 29.74,
3
ꢁ
1
þ
9.725, 24.51; IR: n¼1700 (C¼O) cm ; MS: m/e ¼300 [M] ;
anal. calcd. for C H O S : C 59.96, H 8.05; found: C 59.92, H
15
24
2 2
8
.02.
[
[
8] N. Iranpoor, H. Firouzabadi, M. Shekarrize, Org. Bio-
mol. Chem. 2003, 1, 724.
Acknowledgements
9] Reviews: a) M. Misra, R. Luthra, K. L. Singh, K. Sushil,
in: Comprehensive Natural Products Chemistry; (Eds.:
D. H. R. Barton, K. Nakanishi, O. Meth-Cohn), Perga-
mon: Oxford, 1999; Vol. 4, p. 25; b) J. Staunton, B. Wil-
kinson, Top. Curr. Chem. 1998, 195, 49.
The authors are grateful to Iran TWAS Chapter Based at
ISMO and Shiraz University Grant No: 503614 for the
support of this work.
[
10] a) G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 117;
b) Enantioselective Synthesis of b-Amino Acids, (Eds.:
E. Juaristi), John Wiley & Sons: New York, 1997; c) N.
Sewald, Amino Acids 1996, 11, 397; d) E. Juaristi, H. Lo-
pez-Ruiz, Curr. Med. Chem. 1999, 6, 983; e) P. N. Devine,
R. M. Heid Jr., D. M. Tschaen, Tetrahedron 1997, 53,
6739.
References and Notes
[
1] P. T. Anastas, T. C. Williamson, Eds.; Green Chemistry,
ACS Symposium Series 626; American Chemical Soci-
ety: Washington: DC, 1996, and references cited therein.
660
ꢁ 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
Adv. Synth. Catal. 2005, 347, 655–661