3096-64-8Relevant academic research and scientific papers
Rapid Access to Fluorinated Anilides via DAST-Mediated Deoxyfluorination of Arylhydroxylamines
Gao, Hongyin,Luo, Junfei,Zhang, Zhuyong
supporting information, p. 9332 - 9336 (2021/12/06)
A new strategy for the synthesis of fluorinated anilides in the absence of metals and oxidants has been developed. This deoxyfluorination of N-arylhydroxylamines with diethylaminosulfur trifluoride (DAST) proceeded smoothly under mild conditions, and the
Kinetics and Mechanism of the Bamberger Rearrangement. Part 4. Rearrangement of Sterically Hindered Phenylhydroxylamines to 4-Aminophenols in Aqueous Sulphuric Acid Solution
Sone, Takaaki,Hamamoto, Kazuhiro,Seiji, Yoshiyuki,Shinkai, Seiji,Manabe, Osamu
, p. 1596 - 1598 (2007/10/02)
The rates of the Bamberger rearrangement of sterically hindered phenylhydroxylamines have been determined in aqueous sulphuric acid solution and the substituent effects (in particular, the steric effects) are discussed.The rate constants for phenylhydroxylamines with 2-substituents (Me, Cl, I) satisfied the Taft equation: log krel = ρ*?* - δES with ρ*-1.93 and δ-1.16.The result shows that steric hindrance of the substituents, in addition to the electron-donating effect, has an accelerating effect on the rates of the Bamberger rearrangement.The rate constants for 3-substituted 2-methylphenylhydroxylamines were generally greater than those for 5-substituted 2-methylphenylhydroxylamines.The difference was attributed to the 'buttressing effect' of neighbouring 3-substituents.This is the first example of steric acceleration of the Bamberger rearrangement.
