Direct epoxidation of unprotected olefinic carboxylic acids using HOF-CH3CN

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 531-534

  Rozen, Shlomo ^a   Bareket, Yifat ^a   Dayan, Sharon ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; EPOXIDE;

ARTICLE; DRUG SYNTHESIS;

EID: 0030033654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02180-9     Document Type: Article

References (20)

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13. See for example: Sattler, A.; Haufe, G Liebigs Ann. Chem. 1994, 921. The authors of this paper were unable to epoxidize free acids en route to the synthesis of fluorolactones. They first esterified them and afterwards hydrolyzed them back to the corresponding epoxy acids.
14. Upon completion of the reaction it was poured into bicarbonate solution, most of the acetonitrile evaporated and the aqueous residue slightly acidified. The reaction mixture was then extracted three times with chloroform, washed with water, dried under MgSO4 and the solvent evaporated. The epoxides were the only materials found, but the yield was not considered quantitative since the mass balance was about 90%. With the exception of 8. all epoxides are known in the literature and referenced accordingly. All physical properties are in excellent agreement with the ones published.
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