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RAKHLIN et al.
triethylmethoxystannane by the appropriate arylal-
kanoles [7].
Reaction of triethyl(phenethyloxy)stannane with
N-bromohexamethyldisilazane. The equimolar mix-
ture of 22.9 g (0.07 mol) of triethyl(phenethyloxy)-
stannane and 16.8 g (0.07 mol) of N-bromohexa-
methyldisilazane was charged into a dry reaction tube,
degassed by the freezing/defreezing method, sealed
and irradiated by the UV light for 4 h. The formed
crystalline product was filtered from the liquid phase.
After distillation of the latter, 4.5 g (54%) of hexa-
methyldisiloxane, 5.5 g (49%) of hexamethyldi-
silazane, 10.0 g (50%) of triethylbromostannane, and
7.5 g (89%) of 2-phenyloxirane with bp 74ºС (12 mm
Reaction of trimethyl(benzyloxy)silane with N-
bromohexamethyldisilazane. The equimolar mixture
of 12.6 g (0.07 mol) of trimethyl(benzyloxy)silane and
16.8 g (0.07 mol) of N-bromohexamethyldisilazane
was charged into a dry reaction tube, degassed by the
freezing/defreezing method, sealed and irradiated by
the UV light for 4 h. After opening the tube, 0.6 g
(48%) of ammonia evolved from the reaction mixture
was trapped. The formed crystalline product was
filtered from the liquid phase. After distillation of the
latter, 5.9 g (72%) of hexamethyldisiloxane with bp
100ºС, nD20 1.3774, and 6.7 g (62%) of trimethyl-
bromosilane was obtained. The precipitate purified by
reprecipitation from chloroform into hexane contained
Hg), nD20 1.5632 was obtained. Н NMR of 2-phenyl-
1
oxirane (δ, ppm): 2.8–2.71 m (2Н, –Н2СО–); 3.86–
3.04 m (1Н, –СН–); 7.38-7.18 m (5Н, С6Н5). The
precipitate was separated and purified by reprecipita-
tion from chloroform into hexane; it contained 6.4 g
(30%) of complex [Et3SnBr·NH3] and a polymeric
product.
1
8.2 g (39%) of hydrobenzamide; Н NMR (δ, ppm):
8.57 s (1Н, –CH=N–); 7.86–7.79, m (5Н, С6Н5); 7.4–
7.33 m (10Н, С6Н5–С=N–); 5.94 s (1Н, –CHN2-).
Reaction of trimethyl(3-phenylpropoxy)silane
with N-bromohexamethyldisilazane. The equimolar
mixture of 14.6 g (0.07 mol) of trimethyl(3-phe-
nylpropoxy)silane and 16.8 g (0.07 mol) of N-bromo-
hexamethyldisilazane was charged into a dry reaction
tube, degassed by the freezing/defreezing method,
sealed and irradiated by the UV light for 4 h. After
distillation at atmospheric pressure 3.8 g (46%) of
hexamethyldisiloxane, 9.2 g (82%) of hexamethyl-
disilazane, and 0.1 g (0.5%) of trimethylbromosilane
was obtained. Vacuum distillation gave 7.1 g (35%) of
trimethyl(3-bromo-2-phenylpropoxy)silane with bp
Reaction of triethyl(benzyloxy)stannane with N-
bromohexamethyldisilazane. The equimolar mixture
of 21.9 g (0.07 mol) of triethyl(benzyloxy)stannane
and 16.8 g (0.07 mol) of N-bromohexamethyl-
disilazane was charged into a dry reaction tube,
degassed by the freezing/defreezing method, sealed
and irradiated by the UV light for 4 h. The formed
crystalline product was filtered from the liquid phase.
After distillation of the latter, 2.8 g (34%) of hexa-
methyl-isiloxane, 4.7 g (42%) of hexamethyldisilazane
with bp 35ºС (35 mm Hg), nD20 1.4080 and 12.5 g
(62%) of triethylbromostannane with bp 97ºС (13 mm
Hg), nD20 1.5240 was obtained. The precipitate was
separated and purified by reprecipitation from chloro-
form into hexane; it contained 5.3 g (25%) of hydro-
benzamide and 3.3 g (16%) of complex [Et3SnBr·NH3].
123ºС (2 mm Hg), nD22 = 1.5062; Н NMR (δ, ppm):
1
0.17 s (9Н, Ме3Si); 2.44–2.27 m (2Н, –СН2–); 2.52–
2.48 m (2Н, СН2Ph); 5.74–5.71 m (1Н, –СНBr); 7.58–
7.13 m (5Н, С6Н5).
Reaction of trimethyl(phenethyloxy)silane with
N-bromohexamethyldisilazane. The equimolar mixture
of 13.6 g (0.07 mol) of trimethyl(phenethyloxy)silane
and 16.8 g (0.07 mol) of N-bromohexamethyl-
disilazane was charged into a dry reaction tube,
degassed by the freezing/defreezing method, sealed
and irradiated by the UV light for 6 h. After distillation
at atmospheric pressure 2.6 g (31%) of hexamethyl-
disiloxane, 8.2 g (72%) of hexamethyldisilazane, and
1.1 g (10%) of trimethylbromosilane was obtained.
Vacuum distillation gave 6.9 g (36%) of trimethyl(2-
bromo-2-phenylethoxy)silane with bp 167ºС (3 mm
Hg); 1Н NMR (δ, ppm): 0.1 s (9Н, Ме3Si); 4.15–4.02 t
(2Н, –СН2–); 4.99–4.95 m (1Н, –СНBr–); 7.57–7.23
m (5Н, С6Н5).
Reaction of triethyl(3-phenylpropoxy)stannane
with N-bromohexamethyldisilazane. The equimolar
mixture of 23.9 g (0.07 mol) of triethyl(3-phenyl-
propoxy)stannane and 16.8 g (0.07 mol) of N-bromo-
hexamethyldisilazane was charged into a dry reaction
tube, degassed by the freezing/defreezing method,
sealed and irradiated by the UV light for 8 h. After
distillation 3.2 g (38%) of hexamethyldisiloxane, 6.9 g
(61%) of hexamethyldisilazane, and 9.3 g (47%) of
trimethylbromostannane with bp 97ºС (13 mm Hg),
nD20 1.5240 was obtained. Vacuum distillation gave
8.2 g (88%) of 2-phenyloxetane with bp 91ºС (9 mm
Hg), nD20 1.5456; 1Н NMR (δ, ppm): 3.03–2.53 m (2Н,
–СН2–); 4.83–4.59 m (2Н, –СН2О); 5.82–5.77 m (1Н,
–СН–); 7.29–7.12 m (5Н, С6Н5).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 5 2010