O a-alkylation

This reaction was first reported by Perkin in 1883. It is the nucleophilic alkylation between malonic ester and Q, o)-alkyl dihalide to form cyclic aliphatic 1,1-diester or acid and is known as the Perkin reaction or Perkin synthesis. Although it was once referred to as the Perkin condensation, this name should not be used for this type of reaction. Using this protocol, Perkin successfully prepared cyclopropane-, cyclobutane-, cyclopentane-, cyclohexane-, and cycloheptane-1,1-dicarboxylie acids. However, this reaction is often complicated by the side reaction that forms Q, o, a ,a -tetracarboxylic ester from the Sn2 reaction between malonic ester and o, a -alkyl dihalide, this side reaction can be depressed if alcoholic sodium malonic ester is added slowly to the o, a -alkyl dihalide with vigorous stirring. It is interesting that the K2CO3 promoted a reaction between dimethyl 1,3-acetonedicarboxylate and tran5 -l,4-dibromobutene yields vinyldihydrofuran. ... 

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See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ , ]

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