1642
H. Firouzabadi et al.
LETTER
Table Thioacetalization of Carbonyl Functions, Transthioacetal-
ization of O,O- and S,O-acetals Catalyzed by 1 in CHCl3 at room
temperature
Acknowledgement
The authors are thankful to the Shiraz University Research Council
for the support of this work.
Entry R1
R2
H
H
H
H
H
H
H
H
H
H
H
H
H
X or XX
n
1
2
1
2
1
2
2
2
2
2
1
2
2
Time(h) Yielda,b(%)
1
2
Ph
O
O
O
O
O
O
O
O
O
O
O
O
O
1
95
95
96
94
95
95
94
94
95
94
92
92
93
References and Notes
Ph
1
(1) (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in
Organic Synthesis, 2nd ed.; Wiley: New York, 1991, 178–
207. (b) Hauptmann, H.; Moura, C. M. J. Am. Chem. Soc.
1950, 72, 1405. (c) Seebach, D.; Kolb, M. Chem. Ind.
(London) 1974, 687. (d) Ong, B. S. Tetrahedron Lett. 1980,
4225. (e) Kumar, V.; Dev, S. Tetrahedron Lett. 1983, 24,
1289. (f) Ku, B.; Oh, D. Y. Synth. Commun. 1989, 19, 433.
(g) Ong, B. S.; Chan, T. H. Synth. Commun. 1977, 7, 283.
(h) Chowdhury, P. K. J. Chem. Res., Synop. 1993, 124.
(i) Das, N. B.; Nayak, A.; Sharma, R. P. J. Chem. Res.,
Synop. 1993, 242. (j) Kumar, P.; Reddy, R. S.; Singh, A. P.;
Pandey, B. Tetrahedron Lett. 1992, 33, 825. (k) Villemin,
D.; Labiad, B.; Hammadi, M. J. Chem. Soc., Chem.
Commun. 1992, 1192. (l) Tateiwa, J.; Horiuchi, H.; Uemura,
S. J. Org. Chem. 1995, 60, 4039. (m) Maiti, A. K.; Basu, K.;
Bhattacharyya, P. J. Chem. Res., Synop. 1995, 108.
(n) Patney, H. K. Tetrahedron Lett. 1991, 32, 2259.
(o) Patney, H. K.; Margan, S. Tetrahedron Lett. 1996, 37,
4621.
3
4-(CH3)C6H4
4-(CH3)C6H4
4-(CH3)C6H4
3-(CH3)C6H4
2-(CH3)C6H4
2-(OH)C6H4
4-(Br)C6H4
4-(Cl)C6H4
PhCH=CH
PhCH=CH
1
4
1
5
0.75
0.75
0.75
1
6
7
8
9
1.15
2
10
11
12
13
1
1
1.5
(2) (a) Park, J. H.; Kim, S. Chem. Lett. 1989, 629. (b) Tani, H.;
Masumoto, K.; Inamasu, T.; Suzuki, H. Tetrahedron Lett.
1991, 32, 2039. (c) Gajare, A. S.; Shingare, M. S.; Bandgar,
B. P. J. Chem. Res., Synop. 1998, 452. (d) Firouzabadi, H.;
Iranpoor, N.; Karimi, B. Synlett 1998, 739.
14
15
16
17
18
19
20
21
22
23
24
Ph(CH3)CH
Ph
H
H
H
O
1
2
2
1
2
2
2
1
2
2
1
1.5
0.75
1
92
94
96
95
94
96
92
91
89
88
90c
OCH3
OCH2CH3
Ph
(e) Jnaneshwara, G. K.; Barhate, N. B.; Sudalai, A.;
Deshpande, V. H.; Wakharkar, R. D.; Gajare, A. S.;
Shingare, M. S.; Sukumar, R. J. Chem. Soc., Perkin Trans. 1
1998, 965.
CH3
CH3 OCH3
1.5
1
4-(CH3)C6H4
4-(Cl)C6H4
4-(CH3O)C6H4
4-(CH3)C6H4
PhCH2CH2
Ph
H
H
H
H
O(CH2)3O
O(CH2)3O
S(CH2)2O
S(CH2)2O
2.5
1.5
1.5
1.5
2
(3) (a) Tietze, L. F.; Weigand, B.; Wulff, C. Synthesis 2000, 69.
(b) Saraswathy, V. G.; Sankararaman, S. J. Org. Chem.
1994, 59, 4665.
(4) (a) Corey, E. J.; Shimoji, K. Tetrahedron Lett. 1983, 24,
169. (b) Anand, R. V.; Saravanan, P.; Singh, V. K. Synlett
1999, 415.
(5) Garlaschelli, L.; Vidari, G. Tetrahedron Lett. 1990, 31,
5815.
(6) Olah, G. A.; Narang, S. C.; Meider, D.; Salem, G. F.
Synthesis 1981, 282.
(7) (a) Kamitori, Y.; Hojo, M.; Masuda, R.; Kimura, T.;
Yoshida, T. J. Org. Chem. 1986, 51, 1427. (b) Perni, R. B.
Synth. Commun. 1989, 19, 2383. (c) Muthusamy, S.;
Arulananda Babu, S.; Gunanathan, C. Tetrahedron Lett.
2001, 42, 359. (d) Chandrasekhar, S.; Takhi, M.; Ravindra,
R. Y.; Mohapatra, S.; Rama, R. C.; Venkatram, R. K.
Tetrahedron 1997, 44, 14997. (e) Komatsu, N.; Uda, M.;
Suzuki, H. Synlett 1995, 984. (f) Choudary, B. M.; Sudha,
Y. Synth. Commun. 1996, 26, 2993.
CH3 O(CH2)3O
CH3 O(CH2)3O
2.5
25
26
27
28
29
30
PhCH=CH
H
H
H
C(CH2O)4
2
2
1
2
2
1
1.5
1.5
2
94c
4-(CH3O)C6H4
4-(Cl)C6H4
C(CH2O)4
96c
C(CH2O)4
92c
3,4-(CH3O)C6H3 CH3
O
O
O
12
12
12
30d,e
65d,e
40d,e
PhCH2
Et
(8) (a) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. Synlett
2000, 261. (b) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H.
Synlett 1999, 319. (c) Firouzabadi, H.; Iranpoor, N.; Karimi,
B. Synthesis 1999, 58. (d) Firouzabadi, H.; Karimi, B.;
Eslami, S. Tetrahedron Lett. 1999, 4055.
(9) (a) Ziegler, K. Liebigs Ann. Chem. 1942, 80. (b) Juenge, E.
C.; Spangler, P. L.; Duncan, W. P. J. Org. Chem. 1966, 31,
3836. (c) Juenge, E. C.; Beal, D. A. Tetrahedron Lett. 1968,
5819. (d) Juenge, E. C.; Beal, D. A.; Duncan, W. P. J. Org.
Chem. 1970, 35, 719. (e) Olah, G. A.; Narang, S. C.; Salem,
G. F. Synthesis 1980, 659.
31
32
33
Acetyl ferrocene
Propyl
O
O
O
1
1
1
12
60d,e
87
H
H
3.5
3.5
85
a Isolated yields.
b Structures were confirmed by IR, 1H NMR, 13C NMR, mp/bp.
c 2.2 equiv of dithiol and 0.2 mol of 1 were used.
d 0.15 mol of 1 were used.
e NMR yields.
Synlett 2001, No. 10, 1641–1643 ISSN 0936-5214 © Thieme Stuttgart · New York