Tetrahedron

Métallation et alkylation des thioimidoesters: application en synthèse

S Masson, V Mothes, A Thuiluer

Index: Masson, S.; Mothes, V.; Thuillier, A. Tetrahedron, 1984 , vol. 40, # 9 p. 1573 - 1580

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Citation Number: 18

Abstract

Alkylation of delocalized anions resulting from metallation of N-phenyl thioimidoesters (precursors of dithioesters and thiolesters) takes place on nitrogen with “saturated” thioimidoesters (alkane thiomidates). On the contrary, unsaturated thiomidoesters (α or β- ethylenic, α-arylated) are regioselectively alkylated on the α carbon atom by alkyl or allylic halides. The possibilities for synthesis offered by successive uses of the reactivities of ...