O. D. Gupta, J. M. Shree6e / Tetrahedron Letters 44 (2003) 2799–2801
2801
this paper should be avoided. Appropriate safety pre-
cautions must be observed when these reactions are
carried out.
16. Xu, Q. Z.; DesMarteau, D. D.; Gotoh, Y. Chem. Com-
mun. 1991, 179–181.
17. Witz, M.; DesMarteau, D. D. J. Fluorine Chem. 1991, 52,
7–12.
18. Gupta, O. D.; Kirchmeier, R. L.; Shreeve, J. M. J. Am.
Chem. Soc. 1990, 112, 2383–2386.
Acknowledgements
1
9. Christen, D.; Gupta, O. D.; Kadel, J.; Kirchmeier, R. L.;
Mack, H. G.; Oberhammer, H.; Shreeve, J. M. J. Am.
Chem. Soc. 1991, 113, 9131–9135.
We are grateful to the National Science Foundation
Grant No. CHE-9720365) for support. O.D.G. is
(
appreciative to the University of Rajasthan, Jaipur,
India, for academic leave to carry out this work.
Thanks are due Dr. Gary Knerr for HRMS
measurements.
20. Gupta, O. D.; Kirchmeier, R. L.; Shreeve, J. M. Inorg.
Chem. 2000, 39, 117–120.
2
2
2
2
1. Xu, Q. Z.; DesMarteau, D. D.; Gotoh, Y. J. Fluorine
Chem. 1992, 58, 71–79.
2. Chambers, R. D.; Greenhall, M. P.; Hutchinson, J. Tet-
rahedron 1996, 52, 1–8.
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2
3
1
19
3 3
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d, CH , J=2.5 Hz); F NMR (188 MHz, CDCl ): l
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+
+
+
sity): 152 (M , 35), 117 (M −Cl, 70), 110 (M −COCH ,
2
+
−1
4
1
8
0), 43 (CH CO , 100); IR (KBr plates, cm ): w 2925 vs,
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82 w, 852 w.
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5. C H ClFO (2c): H NMR (200 MHz, CDCl ): l 1.36
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t, CH CH , J=7.1 Hz), 2.46 (d, CH CO, J=2.6 Hz),
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6
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19
.39 (q, CH CH , J=7.3 Hz); F NMR (188 MHz,
3 2
CDCl ): l −123.82 (broad m); MS (EI) m/e (species,
3
+
+
+
intensity): 182 (M , 15), 147 (M −Cl, 35), 139 (M −
CH CO, 39), 43 (CH CO , 100); IR (neat, KBr plates,
cm ): w 2980 vs, 1761, 1618 s, 1362 m, 1256 vs, 1178 s,
029 s, 1150 s, 882 w, 854 w.
7
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3
−
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8
1
1
999, 55, 12431–12477 and references cited therein; (b)
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2
6. C H FO (2g): H NMR (200 MHz, CDCl ): l 1.63 (d,
6
9
2
3
Bailey, W. H., III; Casteel, W. J., Jr.; Syvret, R. G.
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ton, DC, 1995; pp. 133–171.
3
H, J
=21.1 Hz), 2.27 (s, 3H, CH ), 2.29 (s, 3H,
CH ꢀCF
3
3
19
CH3); F NMR (188 MHz, CDCl ): l −157.87 (q); MS
3
+
+
(
EI) m/e (species, intensity): 132 (M , 54.6), 112 (M −
+
+
HF, 40), 90 (M −CH CO, 45), 43 (CH CO , 100); IR
2
3
−
1
(
neat, KBr plates, cm ): w 3137 vs, 2943 s, 1725 s, 1709
vs, 1467 s, 1262 s, 1163 m, 1079 m, 1020 vs, 908 m, 883
s, 773 s.
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2
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8
3
5
2
3
J. Fluorine Chem. 1996, 77, 161–168.
19
2
H), 7.20 (m, 1H), 6.5 (m, 1H); F NMR (188 MHz,
11. Umemoto, T.; Nagayoshi, M.; Adachi, K.; Tomizawa, G.
J. Org. Chem. 1998, 63, 3379–3385.
CDCl ) (CFCl3 external reference): l −114.95 (CF ),
3
2
−
1
−
81.82 (CF ); IR (neat, KBr plates, cm ): w 3088 vs,
3
1
1
2. Banks, R. E. J. Fluorine Chem. 1998, 87, 1–17.
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1672 vs, 1514 m, 1414 s, 1354 s, 1251 s, 921 m, 854 s;
HRMS calcd for C H F O S: 257.9774; found: 257.9757.
9
6, 1737–1755 and references cited therein; (b) Furin, G.
8
3
5
2
1
2
8. C H F O (3m): H NMR (200 MHz, CDCl ): l 7.53 (m,
G. In Methods of Organic Chemistry (Houben-Weyl)
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H.; Tatlow, J. C., Eds.; 1999; Vol. E10a, pp. 432–499.
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3
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3
3
19
1
H), 7.41 (m, 1H), 6.96 (m, 1H); F NMR (188 MHz,
CDCl ) (CFCl3 external reference): l −116.73 (CF ),
3
2
−
1
−
81.82 (CF ); IR (KBr plates, neat, cm ): w 3137 vs,
3
1
1
2943 s, 1693 vs, 1467 s, 1262 s, 1163 m, 1079 m, 1020 vs,
908 m, 883 s, 773 ms; HRMS calcd for C
242.0002; found: 242.0010.
H F O :
8
3 5 3
4
925–4929.