2909-52-6Relevant articles and documents
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Boyer et al.
, p. 770 (1951)
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Kinetic Isotope Effects for Proton Abstraction from Methanol by Polyhalogenomethyl Carbanions. Cleavage of Me3SiCHX2 and Me3SiCX3 by Base in Methanol.
Eaborn, Colin,Stanczyk, Wlodzimierz A.
, p. 471 - 473 (2007/10/02)
The carbanions XxH(3-x)C- (X=Cl or Br; x=2 or 3) generated by base cleavage of Me3SiCH(3-x)Xx (or some related compounds) in MeOH, show a kinetic isotope kH/kD of ca. 1.1 in proton abstraction from methanol, as given by the product ratio XxH(3-x)CH/XxH(3-x)CD observed for reaction in MeOH-MeOD (1:1) at ca. 21 deg C.The low value of the isotope effect is attributed to the fact that the free electron pair in the carbanion is localized on the carbon centre; carbanions derived from acids of acidities comparable with those of X3CH and X2CH2 but in which the electron pair is conjugatively delocalized, show much larger isotope effects.
1-BROMOBICYCLOBUTANES AND STRONG BASES: PRODUCTS AND MECHANISM
Dueker, Axel,Szeimies, Guenter
, p. 3555 - 3558 (2007/10/02)
Treatment of the bromobicyclobutanes 4a - c with LDA led to the formation of the 1,2,3-butatrienes 6 which were isomerized by excess base to the alkynes 8.Reaction of 4c with LDA afforded 8d, indicating that bicyclobut-1(3)-ene 5 was not an intermediate.