2655-68-7Relevant academic research and scientific papers
Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts
Nagasawa, Shota,Sasano, Yusuke,Iwabuchi, Yoshiharu
supporting information, p. 13189 - 13194 (2016/10/30)
Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo- and regioselectivity. Herein, we report a convenient one-pot process for this transformation that involves the unprecedented N-preferential group transfer of N-oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.
Synthesis of new 7-azabicyclo[2.2.1]heptane derivatives
Marco-Contelles, Jose,Gomez-Sanchez, Elena,Samadi, Abdelouahid,Soriano, Elena,Valderas, Carolina,Alvarez-Perez, Monica,Do Carmo Carreiras, Mria
experimental part, p. 56 - 73 (2010/08/20)
The synthesis of new 7-azabicyclo[2.2.1]heptane derivatives has been achieved in a four-step synthetic sequence, starting from readily available cyclohex-3-enecarboxylic acid, Curtius reaction, stereoselective bromination leading to major benzyl(cis-3, tr
Conversion of Aliphatic Amides into Amines with benzene. Scope of the Reaction
Loudon, G. Marc,Radhakrishna, A. S.,Almond, Merrick R.,Blodgett, James K.,Boutin, Raymond H.
, p. 4272 - 4276 (2007/10/02)
The reagent benzene, PIFA, brings about the facile oxidative rearrangement of aliphatic amides to amines in mildly acidic (pH 1-3) mixed aqueous-organic solvents.Aromatic amines are further oxidized by the reagent and therefore cannot be prepared by this method.The rearrangement, which is in effect an "Hofmann rearrangement", occurs with complete retention of configuration in the migrating group, and the rate of the reaction follows approximately the migratory aptitudes of the migrating groups determined for other similar reactions.Isocyanates are intermediates in the rearrangement but are rapidly hydrolyzed to the product amines under the mildly acidic conditions.The acidic conditions protect the product amines from reacting with the isocyanate intermediates and forming ureas.The reaction is accelerated by addition of pyridine to a pH of approximately 3.The scope of the reaction is discussed.
