Summary
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1.
The reactions of the Grignard reagent derived from the “sterically hindered” 3-chloro-2,4-dimethyl-1-pentene with 2,4-dimethyl-3-pentanone, ethyl formate, and amyl butyrate indicate the favorable effect of a double bond in the β-position on the synthesis of highly branched alcohols, which cannot be prepared by reaction with the corresponding saturated haloalkanes.
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2.
It has been shown that the Grignard reagent derived from 3-chlor-o-2,4-dimethyl-1-pentenie differs fundamentally from 2-butenylmagnesium chloride, in that its reaction with 2,4-dimethyl-3-pentanone gives as its main product the alcohol corresponding to the primary form of the alkenylmagnesium halide.
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Ponomarenko, V.A., Tolkacheva, T.Y. Reaction of the grignard reagent from 3-chloro-2,4-dimethyl-1-pentene with 2,4-dimethyl-3-penta none, ethyl formate, and amyl butyrate. Russ Chem Bull 2, 907–912 (1953). https://doi.org/10.1007/BF01167535
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DOI: https://doi.org/10.1007/BF01167535