121726-27-0Relevant articles and documents
Synthese de cetones a partir de N-phenyl imidothioesters et par l'intermediaire de cetenimines
El-Jazouli, Mustapha,Lage, Nadia,Masson, Serge,Thuillier, Andre
, p. 883 - 888 (2007/10/02)
The thermal decomposition of metallated N-phenyl imidothioesters (lithium or magnesium alkylthio-enaminates generated by either deprotonation or 1,4-addition) led to ketenimines which were trapped in situ by organo-lithium or magnesium compounds to give metallated imines, readily hydrolysed into ketones.This sequence allowed the use of imidothioesters as acyl cation equivalents and also successive and regioselective > 1,3-additions of two different organometallics to an α-unsaturated imidothioester.Ar-turmerone, 2,6-dimethyl-2,7-octadien-4-one, iso-artemisia ketone, α-atlantone and other unsymmetrical ketones were synthesized by this procedure.
METALLATION ET ALKYLATION DES THIOIMIDOESTERS: APPLICATION EN SYNTHESE
Masson, S.,Mothes, V.,Thuillier, A.
, p. 1573 - 1580 (2007/10/02)
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 thioimidoester and dithioester functions (allowing in particular two electrophilic additions on two vicinal carbons) are illustrated by syntheses of terpenic compounds lavandual (and lavandulol) and ar-curcumene.
