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Topic: Alphahaloalkylsilanes vs regular alkylhalide, reactivity?  (Read 1511 times)

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Offline rolnor

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Alphahaloalkylsilanes vs regular alkylhalide, reactivity?
« on: November 29, 2016, 04:29:06 PM »
Is a alphahaloalkylsilanes more or less reactive then the corresponding alkylhalide in nucleophilic substitution?

R3SiCH2Cl

VS

R3CCH2Cl

I have looked on Scifinder but I can not see any absolut answer, the alphahaloalkylsilanes can participate in nuchleophile substitution thats clear though.
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Offline wildfyr

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Re: Alphahaloalkylsilanes vs regular alkylhalide, reactivity?
« Reply #1 on: November 29, 2016, 08:34:01 PM »
Hmmm... I would expect the alkyl halide to be more reactive, since the silane is going to be an electron donator, making the methylene less electrophilic.
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