Si–C BOND CLEAVAGE IN N-[(TRIMETHOXYSILYL)METHYL)]AMINE
2557
1974, no. 22, p. 119.
the cleavage of the Si–C bond in the already formed
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compound 2.
The obtained data prove that methanol cannot be
used as a solvent for the synthesis of N-[(trimeth-
oxysilyl)methyl]amine. Now under way is an investiga-
tion of the influence of the structure of the silane,
solvent, and catalyst on the reaction of the Si–C bond
cleavage using spectral and quantum-chemical
methods, which would allow avoiding side reactions in
the synthesis of compounds with the N–C–Si motif
and elaborating new methods of protodesilylation.
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EXPERIMENTAL
NMR spectra were registered on a Bruker DPX-400
spectrometer [400.1 (1H), 79.5 MHz (29Si)] in solutions
in С6D6 using HMDS as an internal reference. All reac-
tions were performed in an argon atmosphere. Methanol
was dried as described in [31]. Liquid ammonia was
evaporated, the gas flow passed through the traps with
NaOH, ammonia was condensed, sodium metal was
dissolved in it and it was recondensed to a dry trap.
Reaction of ammonia with (chloromethyl)tri-
methoxysilane in methanol. In 200 mL of dry
methanol cooled to –50°C ammonia was dissolved and
3.4 g (0.02 mol) of (chloromethyl)trimethoxysilane
was added. The reaction mixture was slowly heated to
room temperature in a sealed vessel and kept for 36–
48 h. Methanol was removed, to the residue pentane
was added, the precipitate was filtered, washed with
pentane, the filtrate was distilled. Fraction with bp
117–119°С was collected and analyzed.
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