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added, and the reaction mixture was stirred for 2.5 h. The
crystals formed were filtered from the solution and dried in
vacuo to produce 0.95 g (65%) of bromide 20, m.p. 107–
110 ꢁC. IR spectrum (CHCl3, m, cmꢀ1): 1500, 1591 (NCO).
1H NMR (CDCl3, d, ppm): 0.85 (3H, SiMe), 2.50 (3H,
CH3CO), 3.10 s (3H, NMe), 3.4 wide (2H, NCH2), 7.2–
7.6 (5H, C6H5). 13C NMR (CDCl3, d, ppm): 45.03
(NCH3); 17.13 [CH3C(O)]; 7.41 (SiMe); 37.30 (NCH2);
174.58 (C@O); 139.93 (Cipso); 132.88 (Cortho); 128.88
(Cpara); 127.55 (Cmeta). 29Si NMR (CDCl3, d, ppm):
ꢀ42.4. Anal. Calc. for C11H16BrNOSi: C, 46.00; H, 5.97;
N, 4.88. Found: C, 45.83; H, 6.00; N, 4.68%.
O. Dannapel, R. Tacke, in: N. Auner, J. Weis (Eds.), Organosilicon
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4.11. 2,2-Dimethyl-3-
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one (21)
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a solution of 2,2-dimethyl-3-(trimethylsilyl)benzo[2H]-1,3-
oxazin-4-one (5 g, 0.02 mol) in hexane (15 ml). The reac-
tion mixture was stirred for 1 h. The crystals formed were
filtered from the solution and dried in vacuo to yield 6 g
(86%) of compound 21, m.p. 139–141 ꢁC (benzene) IR
spectrum (CHCl3, m, cmꢀ1): 1618, 1517 (NCO).
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USSR].
1H NMR (CDCl3, d, ppm): 1.83 s (6H, 2CH3); 0.78 s
3
(3H, SiMe); 2.98, 3.49 dd (2H, JHH 14.2 Hz, NCH2);
3
3
7.79 d (1H, JHH 7.9 Hz, H-5), 7.61 t (1H, JHH 7.9 Hz,
3
3
H-4), 7.16 t (1H, JHH 7.9 Hz, H-3), 7.01 d (1H, JHH
7.9 Hz, H-2), 7.24–7.43 m (5H, C6H5). 13C NMR (CDCl3
d, ppm): 6.51 (SiMe); 35.32 (NCH2); 24.66 (CMe2);
173.28 (C@O); 138.33 (Cipso); 133.58 (Cortho); 127.87
(Cpara); 126.51 (Cmeta) (C6H5); 100.0 (C-1); 138.03 (C-2),
128.38 (C-3), 123.03 (C-4), 117.78 (C-5); 91.55 (C-6);. 29Si
NMR (CDCl3, d, ppm): ꢀ47.2. Anal. Calc. for
C18H20ClO2NSi: C, 62.49; H, 5.83; N, 4.048. Found: C,
62.28; H, 5.73; N, 3.80%.
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Sciences, Moscow, 2003, p. 23.
Acknowledgments
[25] Yu.I. Baukov, Yu.E. Ovchinnikov, A.G. Shipov, E.P. Kramarova,
Vad.V. Negrebetsky, Yu.T. Struchkov, J. Organomet. Chem. 536–
537 (1997) 399.
[26] A.A. Macharashvili, V.E. Shklover, Yu.T. Struchkov, G.I. Oleneva,
E.P. Kramarova, A.G. Shipov, Yu.I. Baukov, J. Chem. Soc., Chem.
Commun. 11 (1988) 683.
The authors are grateful to Prof. Yu.E. Ovchinnikov
and Dr. S.A. Pogozhikh for the X-ray data and to Dr.
A.A. Korlyukov for the assistance in quantum-chemical
calculations (GAUSSIAN-98).
This study was supported by RFBR (Grants 02-03-
32335 and 04-03-32557) and INTAS (Grant 03-51-4164).
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1392 [Russ. Chem. Bull., 2003 (Engl. Transl.)].
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V.E. Shklover, Yu.T. Struchkov, Yu.I. Baukov, Izv. Akad. Nauk,
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