- Nucleophilic cleavage of lactones and esters with zinc selenolates prepared from diselenides in the presence of Zn/AlCl3
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The utility of zinc selenolates for effecting nucleophilic cleavage of simple lactones and esters has been investigated. When zinc selenolate generated via Zn/AlCl3-promoted cleavage of diselenides was reacted with simple lactones and esters, efficient nucleophilic alkyl-oxygen bond cleavage proceeded generating the corresponding carboxylic acids in moderate to excellent yields.
- Nazari, Mohammad,Movassagh, Barahman
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scheme or table
p. 438 - 441
(2009/05/27)
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- Phenyl Selenide Anion, a Superior Reagent for the SN2 Cleavage of Esters and Lactones
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The scope and limitations of SN2-type cleavages of esters and lactones with phenyl selenide anion are discussed.The reagent, when generated properly, is found to be an extremely potent nucleophile.However, its nucleophilicity can be greatly attenuated by varying the counterion and/or the degree of solvation of the anion.The reagent can be used in the presence of a variety of functional groups and exhibits a high degree of selectivity; e.g., methyl esters are selectively cleaved in the presence of ethyl esters.As the hindrance around the carbinol carbon increases, products derived from acyl oxygen cleavage are observed.The mechanistic implications of this are discussed.
- Liotta, Dennis,Sunay, Ustun,Santiesteban, Hector,Markiewicz, William
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p. 2605 - 2610
(2007/10/02)
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