1
1
3
,4-Dimethoxyphenyl-1,3-dithiane (9X ). H NMR (300
1,5-Dithia-spiro[5,5]-undecane (16X ). H NMR (300 MHz,
2
2
MHz, CDCl ) δ 1.94 (m, 1H), 2.16 (m, 1H), 2.90 (m, 2H), 3.05
CDCl ) δ 1.47 (m, 2H), 1.62 (m, 4H), 2.03 (m, 6H), 2.85 (m,
3
3
3
1
(
m, 2H), 3.86 (s, 3H), 3.89 (s, 3H), 5.13 (s, 1H), 6.82 (d, 1H,
4H). C NMR (75 MHz, CDCl ) δ 21.9, 25.7, 25.8, 26.0, 37.8,
3
13
J = 8.4 Hz), 7.02 (m, 2H). C NMR (75 MHz, CDCl ) δ 25.0,
50.2.
3
1
3
2.1, 51.1, 55.8, 110.7, 111.0, 119.9, 131.6, 148.9.
2-Methylphenyl-1,3-dithiolane (17X ). H NMR (300 MHz,
1
1
4
-Acetoxyphenyl-1,3-dithiolane (10X ). H NMR (300 MHz,
CDCl ) δ 2.14 (s, 3H), 3.40 (m, 4H), 7.21 (m, 1H), 7.30 (m, 2H),
1
3
13
CDCl ) δ 2.28 (s, 3H), 3.34 (m, 2H), 3.47 (m, 2H), 5.62 (s, 1H),
7.74 (d, 2H, J = 7.5 Hz). C NMR (75 MHz, CDCl ) δ 33.8,
3
3
13
7
.02 (d, 2H, J = 8.4 Hz), 7.52 (d, 2H, J = 8.4 Hz). C NMR (75
40.2, 68.5, 126.7, 127.0, 127.9, 145.8.
1
MHz, CDCl ) δ 21.1, 40.1, 55.6, 121.5, 129.0, 137.8, 150.2,
2-Methylphenyl-1,3-dithiane (17X ). H NMR (400 MHz,
3
2
1
69.3.
-Acetoxyphenyl-1,3-dithiane (10X ). H NMR (400 MHz,
CDCl ) δ 1.79 (s, 3H), 1.93 (m, 2H), 2.69 (m, 4H), 7.25 (m, 1H),
3
1
13
4
7.37 (m, 2H), 7.93 (d, 2H). C NMR (75 MHz, CDCl ) δ 24.5,
2
3
CDCl ) δ 1.92 (m, 1H), 2.15 (m, 1H), 2.27 (s, 3H), 2.88 (m, 2H),
27.9, 32.7, 53.8, 126.9, 127.6, 128.4, 143.7.
3
1
3
.04 (m, 2H), 5.15 (s, 1H), 7.05 (d, 2H, J = 8.4 Hz), 7.47 (d, 2H,
2,2-Diphenyl-1,3-dithiolane (18X ). H NMR (300 MHz,
1
13
13
J = 8.4 Hz). C NMR (100 MHz, CDCl ) δ 21.0, 24.9, 31.9,
CDCl ) δ 3.39 (s, 4H), 7.27 (m, 6H), 7.59 (m, 4H). C NMR
3
3
5
0.6, 121.7, 128.9, 136.6, 154.4, 169.2.
-Benzoylphenyl-1,3-dithiolane (11X ). Mp 102 ЊC. IR (KBr)
(75 MHz, CDCl ) δ 40.1, 127.2, 127.9, 128.2, 144.6.
3
1
4
2,2-Diphenyl-1,3-dithiane (18X ). H NMR (400 MHz,
1
2
Ϫ1
1
1
736, 1603, 1506, 1270, 1200, 1173, 1068, 1025 cm . H NMR
CDCl ) δ 1.97 (m, 2H), 2.75 (m, 4H), 7.31 (m, 6H), 7.67 (m,
3
13
(
300 MHz, CDCl ) δ 3.36 (m, 2H), 3.50 (m, 2H), 5.66 (s, 1H),
4H). C NMR (100 MHz, CDCl ) δ 24.4, 29.3, 127.5, 128.3,
3
3
13
7
.16 (d, 2H), 7.53 (m, 5H), 8.19 (d, 2H). C NMR (75 MHz,
129.3, 142.4.
CDCl ) δ 40.2, 55.7, 121.6, 122.5, 128.5, 129.1, 130.1, 133.6,
3
1
4
37.8, 151.2, 165.0. Anal. calcd for C H O S : C, 63.54; H,
16 14 2 2
Acknowledgements
.67. Found: C, 63.60; H, 4.71%.
-Benzoylphenyl-1,3-dithiane (11X ). H NMR (300 MHz,
1
4
2
S. N., R. G. and B. K. P. acknowledges the support of this
research to DST New Delhi and CSIR 01(1688)/00/EMR-II
and M. G. to IIT Guwahati. Thanks are due to RSIC, Lucknow
and IIT Kanpur, for providing NMR spectra.
CDCl ) δ 1.93 (m, 1H), 2.16 (m, 1H), 2.90 (m, 2H), 3.06 (m,
2
3
H), 5.19 (s, 1H), 7.19 (d, 2H), 7.41 (m, 1H), 7.51 (m, 3H), 7.64
13
(
m, 1H), 8.18 (d, 2H). C NMR (75 MHz, CDCl ) δ 25.0, 32.0,
3
5
1
0.6, 121.9, 122.5, 128.5, 129.0, 130.1, 133.6, 136.7, 150.7,
64.9.
4
-Benzyloxyphenyl-1,3-dithiolane (12X ). Mp 92 ЊC. IR
References
1
Ϫ1
1
(
(
5
(
KBr) 2916, 1609, 1512, 1251, 1251, 1173, 1013 cm . H NMR
300 MHz, CDCl ) δ 3.28 (m, 2H), 3.46 (m, 2H), 5.02 (s, 2H),
.61 (s, 1H), 6.89 (d, 2H, J = 8.4 Hz), 7.35 (m, 7H). C NMR
75 MHz, CDCl ) δ 40.1, 56.0, 70.0, 114.7, 127.3, 127.9, 128.5,
1
(a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic
Synthesis, 3rd edn, Wiley Sons, New York, 1999; (b)
3
&
13
P. J. Kocieñski, Protecting Groups, Georg Thieme Verlag, New York,
1994; (c) F. A. J. Meskens, Synthesis, 1981, 501; (d ) M. Schelhaas
and H. Waldmann, Angew. Chem., Int. Ed. Engl., 1996, 35, 2056.
3
1
29.1, 132.1, 136.8, 158.5. Anal. calcd for C H OS : C, 66.63;
16 16 2
H, 5.59. Found: C, 66.68; H, 5.57%.
2 (a) E. J. Corey and D. Seebach, Angew. Chem., Int. Ed. Engl., 1965,
4, 1075; (b) E. J. Corey and D. Seebach, Angew. Chem., Int. Ed.
Engl., 1965, 4, 1077; (c) E. J. Corey and D. Seebach, J. Org. Chem.,
1
4
-Benzyloxyphenyl-1,3-dithiane (12X ). H NMR (400 MHz,
2
CDCl ) δ 1.91 (m, 1H), 2.14 (m, 1H), 2.88 (m, 2H), 3.03 (m,
3
1
966, 31, 4097; (d ) D. Seebach, Angew. Chem., Int. Ed. Engl., 1979,
8, 239; (e) D. Seebach, Angew. Chem., Int. Ed. Engl., 1969, 8, 639;
2
7
1
H), 5.03 (s, 2H), 5.12 (s, 1H), 6.92 (d, 2H, J = 8.5 Hz), 7.37 (m,
1
13
H). C NMR (100 MHz, CDCl ) δ 25.0, 32.1, 50.7, 70.0,
3
( f ) D. Seebach, Synthesis, 1969, 17; (g) B.-T. Gröbel and
D. Seebach, Synthesis, 1977, 357; (h) E. L. Eliel and S. S. Morris–
Natsche, J. Am. Chem. Soc., 1984, 106, 2937; (i) J. E. Lynch,
E. L. Eliel and S. S. Morris-Natsche, J. Am. Chem. Soc., 1984, 106,
2943; (j) P. C. B. Page, M. B. van Niel and J. C. Prodger,
Tetrahedron, 1989, 45, 7643; (k) K. Utimoto, A. Nakamura and
S. Motsubara, J. Am. Chem. Soc., 1990, 112, 8189; (l )
Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, New
York, 1991, vol. 3, ch. 1.3; (m) Comprehensive Organic Synthesis, ed.
B. M. Trost, Pergamon, New York, 1991, vol. 1, ch. 2.3; (n)
G. R. Petti and E. E. van Tamelene, Org. React., 1962, 12, 356.
3 R. K. Olsen, and J. O. Currier Jr., The Chemistry of the Thiol Group
ed. S. Patai, John Wiley & Sons, New York, 1974, part 2, p. 519.
14.9, 127.4, 127.9, 128.5, 128.9, 131.5, 136.8, 158.7.
1
4
-O-allylphenyl-1,3-dithiolane (13X ). H NMR (400 MHz,
1
CDCl ) δ 3.34 (m, 2H), 3.50 (m, 2H), 4.52 (m, 2H), 5.30 (m,
3
13
2
H), 5.62 (s, 1H), 6.03 (m, 1H), 6.87 (m, 2H), 7.42 (m, 2H).
C
NMR (100 MHz, CDCl ) δ 40.1, 55.9, 68.8, 114.6, 117.7, 129.0,
3
1
29.4, 131.9, 133.1, 158.3.
-O-allylphenyl-1,3-dithiane (13X ). H NMR (400 MHz,
1
4
2
CDCl ) δ 1.95 (m, 1H), 2.16 (m, 1H), 2.91 (m, 2H), 3.05 (m,
3
2
H), 4.53 (m, 2H), 5.12 (s, 1H), 5.29 (m, 1H), 5.40 (m, 1H), 6.04
13
(
m, 1H), 6.87 (d, 2H), 7.38 (d, 2H). C NMR (100 MHz,
CDCl ) δ 25.0, 32.1, 50.7, 68.8, 114.8, 117.7, 128.9, 130.0, 131.4,
3
4
(a) Y. Mori, Y. Kohchi and M. Suzuki, J. Org. Chem., 1991, 56, 631;
b) S. D. Rychnovsky, Chem. Rev., 1995, 95, 2021; (c) A. B. Smith III,
S. M. Condon and J. A. McCauley, Acc. Chem. Res., 1998, 31, 35.
1
33.1, 158.6.
-Furyl-1,3-dithiolane (14X ). H NMR (300 MHz, CDCl )
(
1
2
1
3
δ 3.30 (m, 2H), 3.44 (m, 2H), 5.62 (s, 1H), 6.28 (m, 2H), 7.36 (s,
5 A. K. Banerjee and M. S. Laya, Russ. Chem. Rev., 2000, 69, 947.
6 (a) L. F. Fieser, J. Am. Chem. Soc., 1954, 76, 1945; (b) W. E. Truce
and F. E. Roberts, J. Org. Chem., 1963, 28, 961; (c) B. S. Ong,
Tetrahedron Lett., 1980, 21, 4225; (d ) V. Kumar and S. Dev,
Tetrahedron Lett., 1983, 24, 1289; (e) M. A. Ceschi, L. de. A. Felix
and C. Peppe, Tetrahedron Lett., 2000, 41, 9695; ( f ) S. Muthusamy,
S. A. Babu and C. Gunanathan, Tetrahedron Lett., 2001, 42, 359.
7 (a) S. Muthusamy, S. A. Babu and C. Gunanathan, Tetrahedron,
2000, 58, 7897; (b) A. Kamal and G. Chouhan, Tetrahedron Lett.,
13
1
H). C NMR (75 MHz, CDCl ) δ 39.1, 47.4, 107.0, 110.3,
3
1
42.5, 154.2.
1
2
-Furyl-1,3-dithiane (14X ). H NMR (300 MHz, CDCl )
2
3
δ 1.97 (m, 1H), 2.12 (m, 1H), 2.94 (m, 4H), 5.22 (s, 1H), 6.34
13
(
m, 1H), 6.40 (m, 1H), 7.36 (s, 1H). C NMR (75 MHz, CDCl3)
δ 25.0, 30.0, 41.8, 107.6, 110.4, 142.0, 151.5.
1
Cinnamyl-1,3-dithiolane (15X ).
H
NMR (200 MHz,
1
2
002, 43, 1347; (c) E. J. Corey and K. Shimoji, Tetrahedron Lett.,
983, 24, 169; (d ) H. Firouzabadi, B. Karimi and S. Eslami,
CDCl ) δ 3.27 (m, 4H), 5.12 (d, 1H), 6.00 (dd, 1H), 6.52 (d, 1H),
3
1
13
7
1
.26 (m, 5H). C NMR (50 MHz, CDCl ) δ 39.8, 52.0, 126.8,
3
Tetrahedron Lett., 1999, 40, 4055.
28.0, 128.7, 129.4, 130.1, 136.2.
8
9
(a) L. F. Tietze, B. Weigand and C. Wulff, Synthesis, 2000, 69;
(b) J. S. Yadav, B. V. S. Reddy and S. K. Pandey, Synlett, 2001, 238;
(c) H. Firouzabadi, N. Iranpoor and B. Karimi, Synthesis, 1999, 58;
(d ) V. G. Saraswathy and S. Sankararaman, J. Org. Chem., 1994, 59,
1
Cinnamyl-1,3-dithiane (15X ). H NMR (200 MHz, CDCl )
2
3
δ 1.88 (m, 1H), 2.11 (m, 1H), 2.88 (m, 4H), 4.80 (d, 1H), 6.25 (dd,
13
1
H), 6.74 (d, 1H), 7.39 (m, 5H). C NMR (50 MHz, CDCl3)
4
665.
(a) G. A. Olah, S. C. Narang, D. Meidar and G. F. Salem, Synthesis,
981, 282; (b) Y. Kamitori, M. Hojo, R. Masuda, T. Kimura and
δ 25.1, 30.1, 47.6, 125.9, 126.6, 128.0, 128.5, 133.3, 136.0.
1
1
,4-Dithia-spiro[4,5]-decane (16X ). H NMR (200 MHz,
1
1
CDCl ) δ 1.41 (m, 2H), 1.62 (m, 4H), 2.00 (m, 4H), 3.28 (s, 4H).
3
T. Yoshida, J. Org. Chem., 1986, 51, 1427; (c) H. K. Patney,
Tetrahedron Lett., 1991, 32, 2259; (d ) H. K. Patney, Tetrahedron
13
C NMR (50 MHz, CDCl ) δ 25.0, 26.2, 38.3, 42.9, 69.2.
3
1
676
O r g . B i o m o l . C h e m . , 2 0 0 4 , 2, 1 6 7 0 – 1 6 7 7