Antimonial analogues of the cacodyl series

The fuming arsenical liquid discovered by L. C. Cadet de Gassicourt in 1760 was subsequently shown by Bunsen, Baeyer and others to contain cacodyl oxide {(CH3 )2 As}2 O and cacodyl {(CH3 )2 As}2 , but antimonial analogues containing the group, (CH3 )2 Sb, have not hitherto been isolated. Of the earliest attempts to prepare organoantimonial derivatives, the most noteworthy are those of Löwig and of Landolt, who obtained respectively triethylstibine and trimethylstibine. These researches demonstrated a characteristic difference between arsenic and antimony in regard to the formation of their organic derivatives; the former element gave rise to secondary and tertiary alkyl compounds, whereas the latter furnished exclusively trialkylated products.