117615-48-2Relevant articles and documents
THE INTERMEDIATES IN THE INTERACTION OF PHENOLS WITH N-BROMOSUCCINIMIDE
Chow, Yuan L.,Zhao, Da-Chuan,Johansson, Carl J.
, p. 2556 - 2564 (2007/10/02)
Phenols react with N-bromosuccinimide to generate 2-bromocyclohexadienone-type intermediates that enolize to 2-bromophenols thermally or photolytically with a wide range of rate constants depending on the parent phenol.A trace amount of acids not only accelerates the rates of the formation and decomposition of the 2-bromodienones, it also promotes the rearrangement of the 2-bromodienones to cross-conjugated 4-bromocyclohexadienones.The enolization of these last compounds affords 4-bromophenols.The occurrence of autocatalysis in dienone decompositions arising from more acidic bromophenols is also established.The reaction is assumed to occur by a bromophilic attack of phenols on the N-Br bond to form unstable hypobromites that rapidly rearrange to the 2-bromocyclohexadienone intermediates.The quantum yield of the photodecomposition of 2-bromo-(2H)-naphthalene-1-one in the vicinity of 365 nm was determined to be unity.