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note
-
The reaction yields of 4-fluorophenol with dialkyl diazenedi-carboxylates 1-3 are lower than those of 2-chlorophenol with the same diazenes. In the case of 2-chlorophenol, the reactions are typical electrophilic aromatic substitutions while 4-fluorophenol fluorophenol follows the reaction pathway proposed in Scheme 4. After radial chromatography of the reaction mixtures, obtained from 4-fluorophenol and dialkyl diazenedicarboxylates, a certain amount of an unidentified dark residue (tar) remains at the baseline (sample line) of the silica gel plate. This is the reason for lower yields of products 9-11 (Table 2, entries 1-3), prepared from 4-fluorophenol, compared to the yields of the same products that were synthesized from 2-chlorophenol (Table 2, entries 5-7).
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78
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1642295338
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note
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3F) takes place.
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