Stibinin

Stibinin is a molecule that is considered to be an organoantimony compound due to it containing carbon, hydrogen, and antimony atoms.

The final product can be isolated, even though the molecule is highly labile.

The first step of this synthesis involves the treatment of penta-1,4-diyne with dibutylstannane as shown in the figure below.

It is noted that other benzene derivatives with one carbon replaced with a group 15 element can be synthesized via a similar synthetic pathway to that which stibinin is synthesized.

Treatment of 1-chloro-1-bismacyclohexa-2,5-diene with a base, such as DBN, can yield the product bismabenzene.

The four different reaction pathways possible from 1,1-dibutyl-1,4-dihydrostannin to form the products arsabenzene, phosphabenzene, bismabenzene, and stibabenzene.
Bond lengths and angles of benzene, pyridine , phosphorine , arsabenzene , stibabenzene, and bismabenzene [ clarification needed ]