Abstract
The reaction of 1,1-dihalo-alkanes with magnesium and magnesium amalgam has been studied. Methylene bromide and iodide yield, under suitable conditions, a stable solution of methylene magnesium halide which easily olefinates aldehydes and ketones affording the corresponding methylenic olefins in good yields. Other alkylidene halides, under the conditions studied, do not give any stable geminal dimagnesium compound although geminal species are probably present during the in situ reaction between alkylidene halides, carbonyl compounds and magnesium amalgam. A general carbonyl olefination scheme taking into account the majority of the known reactions of this kind is proposed.
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