124188-36-9Relevant academic research and scientific papers
Unexpected smiles rearrangement during borane reduction of 2-aryloxy-2-methylpropionamides
Buchstaller, Hans-Peter,Anlauf, Uwe
, p. 639 - 643 (2007/10/03)
2-Nitrophenols spontaneously rearrange during alkylation with 2-bromo-2-methylpropionamide in the presence of cesium carbonate in acetonitrile to the corresponding 2-hydroxy-2-methyl-N-(2-nitrophenyl)propionamides. Upon reduction of 2-aryloxy-2-methylprop
ipso Nitration in p-halophenyl ethers
Clewley, Robin G.,Fischer, Alfred,Henderson, George N.
, p. 1472 - 1479 (2007/10/02)
Addition of nitronium ion ipso to halogen occurs on nitration of the p-haloanisoles in acetic anhydride at -60 deg C.In the cases of p-fluoro- and p-chloro-anisole, addition of the nitronium ion is reversible and only small amounts of ipso products are obtained.With p-bromoanisole nitrodebromination occurs.When p-halophenyl ethers containing a trapping substituent, e.g., 2-(4-chlorophenoxy)-2-methylpropanoic acid, are used as substrates, substantial amounts of the spiro diene with nitro ipso to halogen, e.g., 3,3-dimethyl-8-chloro-8-nitro-1,4-dioxaspirodeca-6,9-dien-2-one, can be isolated.The results demonstrate that extensive ipso attack at the halogen-substituted position is general in the nitration of p-halophenyl ethers.Key words: ipso nitration, ether, diene, p-haloanisole.
