e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Phenyl selenide anion, a superior reagent for the SN2 cleavage of esters and lactones

D Liotta, U Sunay, H Santiesteban…

Index: Liotta, Dennis; Sunay, Ustun; Santiesteban, Hector; Markiewicz, William Journal of Organic Chemistry, 1981 , vol. 46, # 13 p. 2605 - 2610

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Citation Number: 116

Abstract

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 ...

Methyl pivalate Structure

Methyl pivalate

~99%

methylselanylbenzene Structure

methylselanylbenzene

Pivalic acid Structure

Methyl benzoate Structure

Methyl benzoate

~%

methylselanylbenzene Structure

methylselanylbenzene

benzoic acid Structure

Bz-L-Ala-OMe Structure

~%

methylselanylbenzene Structure

methylselanylbenzene

BZ-ALA-OH Structure

Methyl pivalate Structure

Methyl pivalate

Benzeneselenol Structure

~%

methylselanylbenzene Structure

methylselanylbenzene

Pivalic acid Structure

1-Bromodecane Structure

Benzeneselenol Structure

~%

decylselanylbenzene Structure

decylselanylbenzene

delta-Valerolactone Structure

delta-Valerolactone

Benzeneselenol Structure

~%

5-phenylselanylpentanoic acid Structure

5-phenylselanyl...

Benzeneselenol Structure

γ-Valerolactone Structure

γ-Valerolactone

~%

4-phenylselanylpentanoic acid Structure

4-phenylselanyl...

Methyl benzoate Structure

Methyl benzoate

~%

methylselanylbenzene Structure

methylselanylbenzene

benzoic acid Structure

Ethyl benzoate Structure

~%

ethylselanylbenzene Structure

ethylselanylbenzene

benzoic acid Structure

benzyl benzoate Structure

benzyl benzoate

~%

benzylselanylbenzene Structure

benzylselanylbenzene

benzoic acid Structure

1-phenylethyl benzoate Structure

1-phenylethyl b...

~%

Methylbenzylalcohol Structure

Methylbenzylalcohol

benzoic acid Structure

benzyl benzoate Structure

benzyl benzoate

~%

benzylselanylbenzene Structure

benzylselanylbenzene

benzoic acid Structure

benzyl benzoate Structure

benzyl benzoate

Benzeneselenol Structure

~%

benzylselanylbenzene Structure

benzylselanylbenzene

benzoic acid Structure

Ethyl valerate Structure

~%

ethylselanylbenzene Structure

ethylselanylbenzene

Pentanoic acid Structure

Ethyl benzoate Structure

~%

ethylselanylbenzene Structure

ethylselanylbenzene

benzoic acid Structure

Ethyl valerate Structure

Benzeneselenol Structure

~%

ethylselanylbenzene Structure

ethylselanylbenzene

Pentanoic acid Structure

Isoamyl isovalerate Structure

Isoamyl isovalerate

~%

3-Methylbutanoic acid Structure

3-Methylbutanoi...

isopentyl-phenyl selenide Structure

isopentyl-pheny...

Isoamyl isovalerate Structure

Isoamyl isovalerate

Benzeneselenol Structure

~%

3-Methylbutanoic acid Structure

3-Methylbutanoi...

isopentyl-phenyl selenide Structure

isopentyl-pheny...

benzyl benzoate Structure

benzyl benzoate

Benzeneselenol Structure

~%

benzylselanylbenzene Structure

benzylselanylbenzene

benzoic acid Structure

A novel and highly efficient synthetic route to unsymmetrica...

[Cohen, Richard J.; Fox, Daniel L.; Salvatore, Ralph Nicholas Journal of Organic Chemistry, 2004 , vol. 69, # 12 p. 4265 - 4268]

Nucleophilic cleavage of lactones and esters with zinc selen...

[Nazari, Mohammad; Movassagh, Barahman Tetrahedron Letters, 2009 , vol. 50, # 4 p. 438 - 441]

Nucleophilic cleavage of lactones and esters with zinc selen...

[Nazari, Mohammad; Movassagh, Barahman Tetrahedron Letters, 2009 , vol. 50, # 4 p. 438 - 441]

Nucleophilic cleavage of lactones and esters with zinc selen...

[Nazari, Mohammad; Movassagh, Barahman Tetrahedron Letters, 2009 , vol. 50, # 4 p. 438 - 441]

Nucleophilic cleavage of lactones and esters with zinc selen...

[Nazari, Mohammad; Movassagh, Barahman Tetrahedron Letters, 2009 , vol. 50, # 4 p. 438 - 441]