Synthesis and Halochromism of 4- and 6-Styryl-2-aminotropones

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The methylation of 4-styryltropolones with diazomethane afforded two isomers, 2-methoxy-4-styryltropones and 2-methoxy-6-styryltropones. Their reactions with ammonia gave the corresponding 2-amino-4-styryltropones and 2-amino-6-styryltropones, respectively, by normal nucleophilic substitution. Infrared and ultraviolet absorption spectra were measured. The halochromism of 2-aminotropones was also examined, the halochromic shifts being found to be linearly correlated with the Hammett substituent constants.

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