Journal of Organometallic Chemistry p. 49 - 60 (1984)
Update date:2022-08-16
Topics:
Lasocki, Zygmunt
Witekowa, Malgorzata
The rates of solvolysis of some N-phenyl-1-aza-3,5-dioxa-2,4,6-tris(dimethylsilyl)cyclohexanes, substituted in the benzene ring, have been measured spectrophotometrically in methanol containing a small quantity of water.The reaction is subject to general acid catalysis and is inhibited by weak bases.Electron-donating substituents accelerate the solvolysis.The ρ-constant, derived from the linear relation between the logarithms of the rate constants and Hammett ? constants is -1.2 (ρ = -1.0 in a neutral medium).A reverse deuterium isotope effect has been found(kH/kD = 0.82).The proposed mechanism for the Si-N bond cleavage, and the associated ring-opening, involves simultaneous nucleophilic attack of a solvent molecule on silicon and electrophilic assistance by proton transfer from the catalysing acid to the nitrogen.
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