MKSStal
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SN2 with chloroform anion
Do you think, that SN2 can be performed using some alkyl halide, chloroform and hydroxide to deprotonate it?
For example to make 1,1,1-trichloropropane from ethyl halide.
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clearly_not_atara
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No.
But see e.g.:
https://www.sciencedirect.com/science/article/pii/S004040390...
[Edited on 19-7-2018 by clearly_not_atara]
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MKSStal
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Why is it so? Due to chloroform anion decomposition to dichlorocarbene, and further hydrolysis?
In this publication in second case (R2 = Me), product suggests that unsaturated ester has reacted with dichlorocarbene.
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clearly_not_atara
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Not only that, but if you're using an alkyl halide as the electrophile, the whole reaction is competing with dehydrohalogenation. There are a couple
of cases where trichloromethyl is added to aldehydes or Michael acceptors, but not to halides.
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