1614-92-2Relevant articles and documents
An enamine/HB(C6F5)2 adduct as a dormant state in frustrated lewis pair chemistry
Xu, Bao-Hua,Bussmann, Kathrin,Froehlich, Roland,Daniliuc, Constantin G.,Brandenburg, Jan Gerit,Grimme, Stefan,Kehr, Gerald,Erker, Gerhard
, p. 6745 - 6752 (2013)
The enamine piperidinocyclopentene reacts with HB(C6F 5)2 by formation of the C-Lewis base/B-Lewis acid adduct 10. It shows a zwitterionic iminium ion/hydridoborate structure. However, this adduct formation is apparently reversible and may generate the "invisible" frustrated Lewis pair 11 as a reactive intermediate by hydroboration of the enamine C=C bond in an equilibrium situation at room temperature. Consequently, the FLP 11 was trapped by typical FLP reactions, namely by the reaction with dihydrogen to give the ammonium/hydridoborate 12, the acetylene deprotonation products 13 and 14, and simple borane adducts with pyridine (15) and with an isonitrile (17). The products 10 and 12-15 and the isonitrile adduct 17 were characterized by X-ray diffraction. A DFT study determined the thermodynamic features of the 10 a? 11 equilibrium and of a previously discussed reference system (18 a? 19) derived by reacting piperidinocyclohexene with HB(C6F5)2.
Tf2O-Mediated Intermolecular Coupling of Secondary Amides with Enamines or Ketones: A Versatile and Direct Access to β-Enaminones
Liu, Yong-Peng,Zhu, Cheng-Jie,Yu, Cun-Cun,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 7169 - 7174 (2019/11/16)
Based on the Tf2O-mediated intermolecular reaction of secondary amides with enamines derived from ketones, a novel approach to β-enaminones has been developed. The reaction is widely functional group tolerant and highly chemoselective. In the presence of 4 ? molecular sieves, the method can be extended to the one-pot condensation of secondary amides with ketones for NH β-enaminones synthesis.
Synthesis, structure and thermal decomposition of cycloalkanone enamine peroxides
Starostin, Evgenii K.,Khrustalev, Victor N.,Antipin, Mikhail Yu.,Lalov, Andrei V.
body text, p. 334 - 336 (2010/01/18)
Reactions of cycloalkanone enamines with H2O2 gave bis(1-morpholinocyclopent-1-yl)- and bis(1-morpholinocyclohex-1-yl)-peroxides, which were studied by NMR spectroscopy and X-ray diffraction. Thermolysis of bis(1-morpholinocyclohex-1-yl)-peroxide in n-hexane resulted in two major products, viz., cyclohexanone and morpholine.