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Please login to access the full content or check if you have access via4.4.15.2 Method 2: Catalytic Silylation with Trimethyl(pentafluorophenyl)silane
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Lukevics, E.; Pudova, O., Science of Synthesis, (2002) 4, 310.
Silylation of diacetamide (13, R1 = Me) or N-acetylhydrazine 21 by trimethyl(pentafluorophenyl)silane in the presence of a catalytic amount of potassium cyanide–18-crown-6 complex proceeds at 20°C in diethyl ether or acetonitrile, respectively (Scheme 11).[13,20,21] Such processes are initiated by cyanide ions, which generate pentafluorophenyl anions by reaction with the silane. These anions deprotonate 13 (R1 = Me) or 21, and silylation of the deprotonated compounds follows. Monosilyl derivatives 20 (or 22) are formed with an equimolar ratio of reagents, while tautomeric mixtures of compounds 11 and 12 (or 23 and 24) are prepared from a 1:2 ratio of acetyl derivatives and the silane.
Meeeee 88 Meeeeeeee Meeeeeeeee eeee Meeeeeeee(eeeeeeeeeeeeeeeee)eeeeee[88,88,88]
Meeee eee eeee eeeeeeeeee, eeeeeeeeeee(eeeeeeeeeeeeeeeee)eeeeee eeeeee eeee eeeeeeeeeee (88, M8 = Me)[88] ee M-eeeeeeeeeeeeeee 88[88] ee eeee eeeeee 8,8,8-eeeeeeeee-8-eeeeeeeee-8,8-eeeee-8-eee-8-eeeeeeeeeeee-8-eee (88) ee 8,8,8-eeeeeeeee-8-eeeeee-8-eee-8,8-eeeee-8-eeeeeeeeeeeee-8-eee (88), eeeeeeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeee Meeeeeeeee eeee Meeeeeeeeee(eeeeeeeeeeeeeeeee)eeeeee[88,88]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeeeee (8M)-M-Meeeeeeeeeeeeeeee (88):[88]
M eeeeeee ee 88 (M8 = Me; 8.88 e, 88 eeee), Me8MeM8M8 (8.88 e, 88 eeee), eee MMM•88-eeeee-8 eeeeeee (8.88 e) ee Me8M (88 eM) eee eeeeeee eee 88 e ee 88°M. Meeeeeeeeeee eeee eee eeeeeee ee ee eeeeeeeeeee eeee eeee; eeeee: 8.88 e (88%); ee 88–88°M/88 Meee.
8,8,8-Meeeeeeee-8-eeeeeeeee-8,8-eeeee-8-eee-8-eeeeeeeeeeee-8-eee (88):[88]
M eeeeeee ee 88 (M8 = Me; 8.88 e, 88 eeee), Me8Me(M8M8)8 (88.88 e, 88 eeee), eee MMM•88-eeeee-8 eeeeeee (8.88 e) ee MeMM (88 eM) eee eeeeeee eee 8 e ee 88°M. Meeeeee ee eee eeeeeee ee eeeee eee eeeeeeeeee eeeeeeeeeeeeeeeee eeee 88; eeeee: 8.88 e (88%); ee 88–88°M.
References
| [13] | Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 8888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 8888. |
| [20] | Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [21] | Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 888. |
| [22] | Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 8888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 8888. |
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