Question

J. J. Slipshod made two attempts to generate a product that would allow him to observe fluorescence with the dyes in the lab. In his first attempt, he used diethylamine instead of trimethylamine as the catalyst. In the second attempt, he substituted 2,4,6-trimethoxyphenol for 2,4,6-trichlorophenol. None of the dyes fluoresced. Write a mechanism that explains each result.

In the lab, we reacted 2,4,6-trichlorophenol and Et3N to make bis-(2,4,6-trichlorophenyl) oxalate. Then we reacted the oxalate ester with H2O2 and different dyes to observe fluorescence. The dyes used were:

2,3-benzanthracene (naphthacene)

9,10-bis(phenylethynyl)anthracene

Rubrene

9,10-diphenyl anthracene