Abstract
Under suitable reaction conditions 2-phosphorylated 3-chloropropene 1 monoalkylates methoxide, ethoxide, thiocyanate, methyl and ally1 Grignard reagents and acetamidomalonate—the latter reactions leading to 2-phosphorylated 1-butene, 1,5-hexadiene and C-alkylated α-aminoacids. Diethyl malonate and ethyl acetoacetate give mixtures of mono and dialkylated products whereas ethyl cyanoacetate gives only dialkylated product. Acetylacetone gives a dialkylated product - the monoalkylated intermediate undergoing acyl cleavage to give 2-phosphorylated 5-hexene-2-one as the major product. A new simple route for the preparation of 2-phosphorylated 3-halopropenes via a Homer-Wittig reaction between formaldehyde and methylene diphosphonate is described.
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