SCOPUS 정보 검색 플랫폼

Volumn 14, Issue 26, 1973, Pages 2433-2436

Deconjugative alkylation of the enolate anion derived from ethyl crotonate

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002061964 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)96239-2 Document Type: Article

Times cited : (259)

References (11)

1
- 0000453565
- The preparation and reactions of enolate anions derived from α,β-unsaturated esters
- These authors report only methylation and benzylation reactions and apparently did not attempt to dialkylate esters of this type.
- (1972) Tetrahedron Letters , pp. 4249
- Rathke¹ Sullivan²

3
- 84918229072
- P. de Mayo, Interscience, New York
- (1963) , pp. 345
- Zimmerman¹ Rearrangements²

4
- 84918229071
- We thank Professor K. Morokuma of this department for the program used.

5
- 84918229070
- Lithium diisopropylamide (LDA) was prepared by treatment of diisopropylamine with n-butyl-lithium at 4° for 15 minutes. This reagent when properly prepared is colorless to faintly yellow.

6
- 84918229069
- The yields given are for isolated products and are based on the amount of ester used. All compounds exhibited satisfactory spectral and physical properties. The reactions described herein were worked-up in the usual manner using saturated ammonium chloride which is sufficiently acidic to remove the diisopropylamine.

7
- 84918229068
- A number of 2-substituted acrylates also show this Michael addition behavior with LDA.

8
- 84918229067
- The stoichiometry of this complex follows from the observation that a mixture of LDA, 1 equivalent, and HMPA, 0.5 equivalents, when treated with 1 equivalent of ethyl crotonate gives a 1:1 mixture of I and II (94% combined yield). That a complex is involved is suggested by the fact that HMPA (1 equivalent) is not soluble, at −78°, in a 1 molar THF solution of diisopropylamine (1 equivalent), whereas, 1 equivalent of HMPA rapidly dissolves, at −78°, in the same quantity of LDA solution. We are currently developing a number of other uses for this LDA-HMPA complex along with attempting to further characterize this material.

9
- 84918229066
- Gamma alkylation with these reactions is always less than 3% as determined by GLC and Mass Spectra.

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