SUR LES ORGANOMETALLIQUES ISSUS DE THIOAMIDES. I. REACTIVITE AVEC LES ALDEHYDES ET CETONES; STEREOCHIMIE DE LA CONDENSATION AVEC LA t-BUTYL-4 CYCLOHEXANONE ET LE BENZALDEHYDE

Article abstract of DOI:10.1016/S0022-328X(00)86714-5

Organometallic compounds derived from thioamides RCH2CSN(R³)2 condense normally with aldehydes and saturated ketones.Condensation with 4-t-butylcyclohexanone leads predominantly to equatorial attack by the organometallic compound.These results suggest that the organometallic structure is RCH=C(SM)N(R³)2.The stereoselectivity of the reaction with benzaldehyde depends on R and R³; a mechanism for the formation of β-hydroxythioamides is discussed.