We studied the behavior of the following 1,4 and 1,5 diiodides; 2,2'-diiodobiphenyl (1a), 2,2'-diiododiphenylmethane (1b), 2,2'-diiododiphenyl ether (1c) and Z,Z,-4,5-diethyl-3,6-diiodo-3,5-octadiene (1d) under conditions of photolysis with UV light.  We report in this presentation the formation of five-member ring iodonium salts; 4a and 4d, from the 1,4-diiodides, 1a and 4a.  The tetraethyliodolium salt (4d) is the first non-annulated, non-phenylated iodolium salt and is of particular interest because of its potential aromaticity.  In contrast, the 1,5-diiodides, 1b and 1c did not react to form cyclic iodonium salts.  These results are interpreted in terms of the stability and potential aromaticity of intermediate cyclic 9-I-2 radicals (3).