132. Chemiluminescent organic compounds. Part IV. Amino- and hydrazino-cyclophthalhydrazides and their relative luminescent power

4,7-Diaminoisoindoline-1,3-dione

“…3,4 We repeated this sequence on a small scale to get all of these compounds with physical and spectral properties identical to those reported. 2–4 Subsequent reaction of 3,6-dichlorophthalic anhydride with excess aq NH 3 and CuI (sealed tube, 120–130°C, 8 h) according to the literature procedure, 1 however, gave a product that melted at 273–275°C, which did not match the reported value. Spectral analysis of this material suggested that it was 4-amino-7-chloroisoindoline-1,3-dione rather than the diamino compound.…”

“…This compound has been previously reported from the known 4,7-dichloroisobenzofuran-1,3-dione (also 3,6-dichlorophthalic anhydride). 1 The preparation of this anhydride involved zinc promoted hydrodechlorination of 3,4,5,6-tetrachlorophthalic anhydride under basic conditions to initially give 3,4,6-trichlorophthalic acid. 2–4 Further dechlorination with zinc generated 3,6-dichlorophthalic acid, 2–4 and boiling in toluene with azeotropic removal of water gave 3,6-dichlorophthalic anhydride.…”

The luminescence of biological systems; proceedings of the conference on luminescence, March 28-April 2, 1954, sponsored by the Committee on Photobiology of the National Academy of Sciences-National Research Council and supported by the National Science Foundation

“…Substituents in the benzene ring have a marked effect on the intensity of the chemiluminescence ( Drew and Pearman, 1937;Zellner and Dougherty, 1937). The effect of these substituents on the intensity of the chemiluminescence could almost be predicted on the basis of their effect on fluorescence yields.…”

The Chemistry of the Phthalazines.

“…These substances are structurally the same as the ordinary phthalhydrazides, and their synthesis is achieved by the same general procedures (c/. Section IV and references 42,44,46,83,178,189,193,196).…”

“…Í One maximum in 0.1 N sodium hydroxide (196). § Prepared from 6,7-dichlorophthalhydrazide with ammonia and cuprous iodide (46). presence of reducing agents (91), and similar tests for the presence of traces of ferrous, cobaltous, and cupric ions, and, with suitable precautions, blood (63,123,161,162).…”