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6859
23.48, 68.25 (d, JZ28.5 Hz), 91.03 (d, JZ213.2 Hz),
References and notes
152.03, 168.92 (d, JZ2.2 Hz); MS m/z 147 (MC), 127
(MCKHF), 119 (MCKCO), 106 (MCKCOCH); HRMS
(m/z) calcd for C5H6FNO3 147.0332, found 147.0332.
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3.4.2. 3-Methoxycarbonyl-4-fluoro-2-oxazolidinone (5a).
Yellow oil; 1H NMR (CDCl3) d 3.92 (s, 3H), 4.50 (m, 2H),
6.44 (dd, JZ65.6, 4.3 Hz, 1H); 19F NMR (CDCl3) d
K58.27 (ddd, JZ65.8, 35.1, 22.1 Hz); 13C NMR (CDCl3) d
54.57, 68.02 (d, JZ27.9 Hz), 92.69 (d, JZ215.2 Hz),
149.56 (d, JZ3.3 Hz), 150.13 (d, JZ2.2 Hz); MS m/z 163
(MC), 143 (MCKHF), 133 (MCKOCH2), 105 (MCK
COOCH2); HRMS (m/z) calcd for C5H6FNO4 163.0281,
found 163.0269.
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3.4.3. 3-(4-Fluorophenoxycarbonyl)-2-oxazolidinone
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1
(5b). Yellow oil; H NMR (CDCl3) d 4.04 (t, JZ8.1 Hz,
2H), 4.41 (t, JZ8.1 Hz, 2H), 6.32 (m, 2H), 6.68 (m, 2H); 19F
NMR (CDCl3) d K18.55 (dm, JZ63.8 Hz); 13C NMR
(CDCl3) d 43.30, 61.69, 128.40–130.04 (6c, arom, m),
146.88, 151.04; MS m/z 225 (MC), 181 (MCKCO2);
HRMS (m/z) calcd for C10H8FNO4 225.0437, found
225.0438.
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3.4.4. 3-(C)-Menthoxycarbonyl-4-fluoro-2-oxazolidi-
none (5c). White solid, mp 119–120 8C; 1H NMR
(CDCl3) d 0.79 (d, JZ7.0 Hz, 3H), 0.91 (d, JZ7.0 Hz,
3H), 0.92 (d, JZ6.2 Hz, 3H), 1.01–2.13 (m, 9H), 4.44 (dd,
JZ25.4, 3.0 Hz, 2H), 4.83 (m, 1H), 6.39 (dd, JZ66.2,
4.1 Hz, 1H); 19F NMR (CDCl3) d K57.46 (ddd, JZ65.8,
33.3, 22.1 Hz, 0.5F), K57.78 (ddd, JZ65.8, 33.3, 22.1 Hz,
0.5F); 13C NMR (CDCl3) d 16.31, 20.85, 22.01, 23.32,
26.33, 31.47, 34.02, 40.40, 46.87, 67.49, 79.18, 90.94, 94.12
(2C); MS m/z 138 (MCKC(O)OCH2CHFNC(O)OH); Anal.
Calcd for C14H22FNO4: C, 58.52; H, 7.72; N, 4.87. Found:
C, 58.37; H, 7.31; N, 4.80.
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3.4.5. 3-Fluoromethyloxazolidine-2,4-dione (7b). Yellow
1
oil; H NMR (CDCl3) d 4.82 (s, 2H), 5.61 (d, JZ50.8 Hz,
2H); 19F NMR (CDCl3) d K102.07 (t, JZ50.8 Hz); 13C
NMR (CDCl3) d 67.99 (d, JZ12.3 Hz), 88.65 (d, JZ
214.8 Hz), 158.40, 168.54, MS m/z 133 (MC), 114 (MCK
F), 105 (MCKCO); HRMS (m/z) calcd for C4H4FNO3
133.0175, found 133.0163.
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3.4.6. Oxazolidine-2,4-dione (6a),20a 3-methyloxazoli-
dine-2,4-dione (6b)20b, 3-benzyloxazolidine-2,4-dione
(6d)20c, and 4-fluorophenol (8). The compounds were
19. (a) Umemoto, T.; Tomizawa, G. Bull. Chem. Soc. Jpn. 1986,
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1
indentified by their H NMR and MS spectroscopy.
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J. Am. Chem. Soc. 1945, 67, 522–523. (b) Spielman, M. A.
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Acknowledgements
This research was supported by a Grant-in-Aid for Scientific
Research on Priority Areas (A) ‘Exploitation of Multi-
Element Cyclic Molecules’ from the Ministry of Education,
Culture, Sports, Science and Technology, Japan.