Aniline 2,4-diiodo

Double cyclization in one step is also possible with the l,5-diiodo-2,4-bis(iodomethyl)-pentane precursor. Following that route, the treatment of the precursor with aniline leads to the A, A -diphenyl substituted bispidine 77 (106), whereas the reaction of the tetraiodo compound with 1-phenylethylamine yields the bispidine 78 (Scheme 7) (107). 

An illustration of the molecule, l,l dinitro-2,2-diphenylaminoetbylene [26] is seen in Fig. 17. It is apparent that this molecule could be synthesized from l,l diiodo-2,2-dinitroethylene and aniline. The dinitro plane is twisted 71° from the N-C-N plane at the amino end of the double bond. The phenyl groups are twisted 40 and 60 from the N-C-N plane. 

A synthesis of phthalimides via double carbonylative coupling of ortho-diiodo arenes with anilines has also been reported [98]. The conversion of 149 to 150 proceeded in good yield using a Pd/PPh3-based catalyst system (Eq. (1.59)). 

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