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M. Narendra Mallya et al. / Tetrahedron Letters 42 (2001) 2565–2568
5. For the generation of NOCl using TMSCl and organic or
C10H20ClNOSi: C, 51.48; H, 8.65; N, 6.01. Found: C,
51.43; H, 8.77; N, 6.17. Compound 10: mp 85–87°C. H
1
inorganic nitrites, see: (a) Weiß, R.; Wagner, K. G.;
Hertel, M. Chem. Ber. 1984, 117, 1965; (b) Haub, K. E.;
Lizano, A. C.; Noble, M. E. Inorg. Chem. 1995, 34, 1440.
6. Brief experimental procedure: A well-stirred mixture of
cyclic vinylsilane (10 mmol) and iso-amylnitrite (12.5
mmol) at −15°C was treated dropwise with TMSCl (12.5
mmol). After the disappearance of the vinylsilane (moni-
tored by GC), the solid dimeric primary adduct formed
was filtered rapidly, washed with cold ethanol (5 mL) and
dried. The filtrate was worked up in the usual manner
and the secondary products were separated by silica gel
chromatography (dichloronitroso compounds were eluted
with pure petroleum ether, bp 40–60°C and a-chloro-
ketones formed in aqueous conditions were eluted with
1% ethyl acetate in petroleum ether). All new compounds
were characterized by satisfactory elemental analysis and
spectral data. The known products were identified by
comparing their properties with those reported in the
literature and in many cases with authentic compounds
prepared from known procedures.
7. Selected characterization data (NMR spectra were taken
in CDCl3). Compound 7: mp 110–112°C. 1H NMR
(dimer): l 5.81 (t, J=8.0 Hz, 1H), 2.7 (m, 1H), 2.18 (m,
2H), 1.6–1.9 (m, 3H), 0.1 (s, 9H). 13C NMR: l 69.68,
66.94, 38.76, 27.73, 21.17, −3.17. Anal. calcd for
C8H16ClNOSi: C, 46.70; H, 7.84; N, 6.81. Found: C,
46.71; H, 8.12; N, 6.83. Compound 9: mp 90–92°C. 1H
NMR (monomer–dimer mixture in solution): l 5.87 (dd,
J=1.8 Hz, 2.1 Hz, dimer), 4.33 (dd, J=2.4 Hz, 1.8 Hz,
monomer) (together 1H), 2.13–2.64 (m, 3H), 1.57–1.96
(m, 7H), 0.19 (s), 0.16 (s) (together 9H). Anal. calcd for
NMR (monomer–dimer mixture in solution): l 6.01 (m,
dimer), 4.6 (m, monomer) (together 1H), 2.1–2.7 (m, 4H),
1.5–1.9 (m, 8H), 0.25 (s), 0.15 (s) (together 9H). Anal.
calcd for C11H22ClNOSi: C, 53.31; H, 8.95; N, 5.65.
Found: C, 53.32; H, 9.23; N, 5.92. Compound 11 could
not be fully characterized because of its poor yield and
difficulty in its purification. Compound 12: mp 150–
1
152°C. H NMR (dimer): l 4.93 (s, 1H), 2.73 (broad s,
1H), 2.5 (m, 2H), 1.2–1.7 (m, 5H), 0.3 (s, 9H). 13C NMR:
l 74.88, 68.12, 50.43, 41.33, 38.08, 26.37, 25.59, −0.67.
Anal. calcd for C10H18ClNOSi: C, 51.95; H, 7.79; N,
6.06. Found: C, 51.97; H, 7.90; N, 6.16.
8. (a) Duboudin, F. J. Organomet. Chem. 1979, 174, C18–
C20; (b) Grayson, E. J.; Whitham, G. H. Tetrahedron
1988, 44, 4087.
9. Seyferth, D.; Kahlen, N. Z. Naturforsch. 1959, 14b, 137.
10. Cook, E.; Moerck, R.; Schwindeman, J.; Magnus, P. J.
Org. Chem. 1980, 45, 1046.
11. Patil, G. S.; Nagendrappa, G. Chem. Commun. 1999,
1079.
12. The authors thank the referee for this suggestion.
13. (a) Meinwald, J.; Meinwald, Y. C.; Baker, T. N. J. Am.
Chem. Soc. 1964, 86, 4074; (b) Brown, H. C.; Kawakami,
J. H.; Liu, K. T. J. Am. Chem. Soc. 1973, 95, 2209; (c)
Nelson, D. J. Tetrahedron Lett. 1999, 40, 5823.
14. Kyung, J. H.; Clappa, L. B. J. Org. Chem. 1976, 41,
2024.
15. Ponder, B. W.; Walker, D. R. J. Org. Chem. 1967, 32,
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