In a search for convenient preparative techniques, we have investigated the effect of solvent, halide, base, and temperature on the alkylation of the ambldent anion derived from ethyl acetoacetate. Our attention has focused on the use of dipolar aprotic solvents. A recent report (1) describing oxyge
The alkyl group effect in the alkylations of ethyl acetoacetate in dimethyl sulfoxide
β Scribed by W.J. le Noble; J.E. Puerta
- Publisher
- Elsevier Science
- Year
- 1966
- Tongue
- French
- Weight
- 164 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Recent insights (1) in the remarkable solvent properties of dimethyl eulfoxida (DMSO), and our own interest in the chemistry of isopropcnyl ethers (2) led u8 to consider the poraibility of direot 0-alkylation of ethyl aoetoaoetate in that solvent. The connection i# that Kornblum'rr work (3) suggests increaasd &alkylat.ion of ambidmt anions when the oxygen atcrP is strongly solvated, and that cations mther
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retarding effect of alkali metal and alkaline-earth metal ions on the rate of intramolecular 0-alkylation of the title compound has been thoroughly investigated in 99% aqueous Me2SO at 25-C. Rate data have been dissected into contributions of free ions (ki) and ion pairs (k. ). Xl Comparison of the