Aspects of the chemistry of halophenols and halodienones

The intermediates in the interaction of phenols with N-bromosuccinimide

“…While equally compatible with a hexadienone structure, i.e., structhese data, as well as the uv absorption parameters (Table l), tures analogous to those of 3 and 4 (vide infra) (4,12,13). Since were consistent with the intermediates possessing dienone-type the reaction of NBS with phenols is a simple and clean method structures (12,13), they failed to exclude the possibility of preparing monobromo derivatives of phenols, and some of of hypobromite intermediates, since alkyl hypobromites are their intermediates can be developed as secondary actinometers, reported to show absorptions near 340 nm (14,15).…”

“…lb). Under the dark, ambient prototype electrophilic reaction (4)(5)(6)(7)(8). NBS has been used as conditions, the new product from 1-NpOH decomposed slowly, an analytical reagent for phenols such as vanillin and thymol and completely in a few days, to give 2-bromo-1 -naphthol 5 and (9, lo), but its mechanistic aspects have scarcely received any a small amount of the 4-bromo isomer 6.…”