Synthesis and structures of triphenylantimony oximates

The reactions of triphenylantimony or trimethylantimony with tert-butyl hydroperoxide in the presence of acetone oxime, acetophenone oxime, cyclohexanone oxime, or benzaldehyde oxime afforded monomeric triorganoantimony oximates Ph3Sb(ON=CMe2)2, Ph3Sb(ON=CMePh)2, Ph3Sb[ON=C(CH2)5]2, Ph3Sb(ON=CHPh)2, and Me3Sb(ON=CMe2)2 in 87—96% yields. X-ray diffraction analysis demonstrated that Ph3Sb(ON=CMe2)2 and Ph3Sb(ON=CHPh)2 have trigonal-bipyramidal structures. An analogous reaction with dimethylglyoxime gave rise to polymeric triphenylantimony dioximate in 96% yield. The reaction with butane-2,3-dione monoxime yielded chelate cyclic bis(triphenylantimony) oxides.