4-iodo-4 -nitrobiphenyl

Some subsequent discussion on compound 3 followed our original paper on this subject (N. Masciocchi, M. Bergamo, A. Sironi, Comments on the elusive crystal structure of 4-iodo-4 -nitrobiphenyl Chem. Comm, 1998,1347-1348 J. Hulliger, P. J. Langley, On intrinsic and extrinsic defect-forming mechanisms determining the disordered structure of 4-iodo-4 -nitrobi-phenyl Chem Comm, 1998, 2557-2558), but these papers, which describe the effects of small amounts of 4,4 -dinitrobiphenyl impurity in 3, only reinforce the idea of structures based on N02—I synthons. 

Figure 8.3 Crystal packing using the nitro/iodo supramolecular synthon (a) antiparallel, centro-symmetric packing in 4-nitroiodobenzene, (b) non-linear optical active parallel arrangement of polar stacks in 4-iodo-4 -nitrobiphenyl.4...

Iodo-3-nitrobiphenyl 26 could be converted to the iodonium iodide 27 in 75 % yield via standard procedure. Upon heating with copper(I) oxide at 300—340 °C, 0.56% yield of 1,16-dinitrotetraphenylene 28 as well as 1-nitrobiphenylene 2P were isolated (Eq. 11)... 

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