Tetrahedron

Preparation and Oxidation of α-Phenylselanyl Esters

L Lebarillier, F Outurquin, C Paulmier

Index: Lebarillier, Loic; Outurquin, Francis; Paulmier, Claude Tetrahedron, 2000 , vol. 56, # 38 p. 7483 - 7493

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Citation Number: 18

Abstract

Alkylation and selenenylation of selenium-stabilized ester enolates have allowed the preparation of α-phenylselanyl esters 5, 7, 8 and of α, α-bis (phenylselanyl) esters 6, respectively. The competitive selenophilic reaction, leading to an allylic phenylselenide 9, was avoided in the presence of HMPA. α-phenylselanyl α, β-unsaturated esters 15 were prepared by oxidation of compounds 6 and dehydrohalogenation of β-chloroesters 17. ...