Molecular Design based on the characteristics of heteroatoms

Triarylbismuthanes 1a, c fully substituted with arenes each bearing a p-accepting substituent such as ester and cyano group, which are inaccessible by a conventional Grignard method, were synthesized by using the iodine-magnesium exchange of iodoarenes with isopropylmagnesium bromide. Furthermore, a convenient route to 1d using the iodine-lithium exchange of 4-iodonitrobenzene with phenyllithium was developed. Bismuthane 1b was obtained by hydrolysis of 1a under alkaline conditions. Construction of three-dimensional organometallics based on the supramolecular interaction in the crystalline states was attempted by using 1b, c and 1d.