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Patz, Matthias and Mayr, Herbert (1993): How nucleophilic are silyl enol ethers? Kinetics of the reactions of electron rich CC-double bonded systems with carbenium ions. In: Tetrahedron Letters, Vol. 34, No. 21: pp. 3393-3396 [PDF, 248kB]


Rate constants for the reactions of the bis(p-dimethylaminophenyl)carbenium ion 1 with silyl enol ethers, allyl silanes, and allyl stannanes show the reactivity order H2C=CR-CH2SiMe3 < H2C=CR-OSiMe3 < H2C=CR-CH2SnBu3.

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