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4399
3. Raasch, M. S. In Thiophene and its Derivatives; Gronow-
itz, S., Ed.; John Wiley & Sons: New York, 1985; p. 571.
4. Gronowitz, S. Phosphorus, Sulfur, Silicon 1993, 74, 113.
5. Nakayama, J.; Sugihara, Y. Top. Curr. Chem. 1999, 205,
131.
was allowed to stand at rt until the substrate was con-
sumed (TLC). All volatile materials were evaporated in
vacuo, finally at 0.5–1 mmHg, and the residue was recrys-
tallized from hexane–CH2Cl2, yielding 12.5 g (82%) of
2,5-dibromothiophene-1,1-dioxide.
6. (a) Barbarella, G.; Pudova, O.; Arbizzani, C.; Mas-
tragostino, M.; Bongini, A. J. Org. Chem. 1998, 63, 1742;
(b) Arbizzani, C.; Barbarella, G.; Bongini, A.; Favaretto,
L.; Mastragostino, M.; Ostoja, P.; Pudova, O.; Zam-
bianchi, M. Opt. Mater. 1998, 9, 43–45; (c) Barbarella,
G.; Favaretto, L.; Zambianchi, M.; Pudova, O.; Arbiz-
zani, C.; Bongini, A.; Mastragostino, M. Adv. Mater.
1998, 10, 551; (d) Yamamoto, T.; Nurulla, I.; Hayashi,
H.; Koinuma, H. Synth. Metals 1999, 107, 137–141.
7. Rosen, S.; Bareket, Y. J. Org. Chem. 1997, 62, 1457–
1462.
8. Miyahara, Y.; Inazu, T. Tetrahedron Lett. 1990, 31,
5955–5958.
9. Nenajdenko, V. G.; Krasovskij, A. L.; Lebedev, M. V.;
Balenkova, E. S. Synlett 1997, 12, 1349.
10. (a) Pouzet, P.; Erdelmeier, I.; Ginderow, D.; Mornon,
J.-P.; Dansette, P.; Mansuy, D. J. Chem. Soc., Chem.
Commun. 1995, 473; (b) Pouzet, P.; Erdelmeier, I.; Gin-
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Heterocycl. Chem. 1997, 34, 1567.
The NMR spectra and melting points for all known
substances are in accordance with literature data.
1: White crystals, mp 147–150°C (dec.). 1H NMR (400
MHz, CDCl3) 3.25 (s, 3H, SO2CH3); 7.25 (d, 1H, J=5.0
Hz); 7.65 (d, 1H, J=5.0 Hz); 13C NMR (400 MHz,
CDCl3) 45.05 (CH3), 118.08 (CH), 123.46 (CH), 127.32
(C), 141.16 (C). Found: C, 21.96; H, 1.89. Anal. calcd for
C5H5O4SBr: C, 21.99; H, 1.85%.
1
5: White crystals, mp 123–124°C. H NMR (CDCl3) 3.25
(s, 3H); 7.08 (d, 1H, J=8.0 Hz); 7.70 (d, 1H, J=8.0 Hz);
13C NMR 45.53 (CH3), 118.52 (CH), 123.58 (CH), 138.36
(C), 140.98 (C). Found: C, 26.18; H, 2.16%. Anal. calcd
for C5H5O4SCl: C, 26.26; H, 2.20%.
8: Pale yellow crystals, mp 60–62°C. 1H NMR (CDCl3)
7.11 (s, 1H); 13C NMR 118.40 (CH), 121.67 (C), 129.03
(C), 131.44 (C). Found: C, 18.25; H, 0.35%. Anal. calcd
for C4HCl2Br: C, 18.20; H, 0.38%.
14. Barbarella, G.; Favaretto, L.; Sotgiu, G.; Zambianchi,
M.; Antolini, L.; Pudova, O.; Bongini, A. J. Org. Chem.
1998, 63, 5497.
11. Ho, M. T.; Treiber, A.; Dansette, P. Tetrahedron Lett.
15. Highly concentrated H2O2 was obtained according to:
Giguere, P. A. Bull. Chem. Soc. Fr. 1954, 720, and stored
at −20°C as a 5 M solution in CH3CN. This solution
seems to be quite stable at this temperature and did not
show any signs of decomposition while being kept even at
room temperature. Special care should be taken while
handling anhydrous H2O2 and we recommend minimiz-
ing the time of storing it in the pure form.
1998, 39, 5049–5052.
12. Lu, Y.; Lemal, D. M.; Jasinski, J. P. J. Am. Chem. Soc.
2000, 122, 2440–2445.
13. Typical procedure: An equimolar quantity of tri-
fluoroacetic anhydride (26.2 g, 17.5 ml) was cautiously
added to an ice-cold solution of H2O2 (0.125 mol) in
100 ml of CH3CN. After 1 h, 12.1 g (0.05 mol) of
2,5-dibromothiophene was added at 0°C. The mixture
15
.