Journal of the Chemical Society. Chemical communications p. 1289 - 1290 (1985)
Update date:2022-08-16
Topics:
Dembech, Pasquale
Eaborn, Colin
Seconi, Giancarlo
The reaction of 5-nitro-2-(trimethylsilylmethyl)thiophene with NaOMe-MeOH involves generation of the observable anion <5-O2N*C4H2S*CH2>(1-) with a solvent isotope effect k(MeOH)/k(MeOD) of 0.5, followed by protonation of the anion with a solvent isotope effect of 10; the results confirm that cleavages of RSiMe3 compounds by NaOMe-MeOH involve separation of the anions R(1-), and that the isotope effect in the reaction of R(1-) with MeOH depends greatly on the degree of conjugative delocalization of the negative charge, not just on the acidity of RH.
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