92-29-5Relevant articles and documents
Resolution of Enantiomers of Novel C2-Symmetric Aminobisphosphinic Acids via Diastereomeric Salt Formation With Quinine
Kaboudin, Babak,Faghihi, Mohammad-Reza,Kazemi, Foad,Yokomatsu, Tsutomu
, p. 71 - 74 (2015)
C2-symmetric N,N-bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C2-symmetric N,N-bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation with (-)-quinine, and subsequent fractional crystallization. X-ray crystallographic analysis of one of the diastereomeric salts clearly revealed that (-)-quinine could be an efficient resolving agent for obtaining the single enantiomer (R,R)-N,N-bis(phosphinomethyl)amine.
Reactions of dialkyl phosphonates and phosphinates with bis(benzylideneimino)toluene
Pudovik,Shagidullin,Khairullin,Vandyukova,Chernova,Gainullin,Pudovik
, p. 1242 - 1244 (1996)
Dialkyl phosphonates bind to the C=N bond of bis(benzylideneimino)toluene, with formation of dialkyl (benzylideneimino)benzylaminobenzyl phosphonates. The complicated character of IR spectra of these compounds is connected with the possibility of formation of dimeric cyclic associates and intramolecular hydrogen bonding. Phosphinic acid reacts with bis(benzylidenimino)toluene in a 2 : 1 ratio to afford N,N′-benzylidenebis(α-amino-benzylphosphonic) acid.
Synthesis of β-Phosphinolactams from Phosphenes and Imines
Fu, Xingyang,Li, Xinyao,Xu, Jiaxi
supporting information, p. 8733 - 8737 (2021/11/17)
Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states to give final cis-β-phosphinolactams. C-Styrylimines generally give rise to β-phosphinolactams in higher yields than C-arylimines. The stereoselectivity and proposed mechanism are rationalized by DFT theoretical calculation.
A Journey from Thermally Tunable Synthesis to Spectroscopy of Phenylmethanimine in Gas Phase and Solution
Melli, Alessio,Potenti, Simone,Melosso, Mattia,Herbers, Sven,Spada, Lorenzo,Gualandi, Andrea,Lengsfeld, Kevin G.,Dore, Luca,Buschmann, Philipp,Cozzi, Pier Giorgio,Grabow, Jens-Uwe,Barone, Vincenzo,Puzzarini, Cristina
supporting information, p. 15016 - 15022 (2020/10/19)
Phenylmethanimine is an aromatic imine with a twofold relevance in chemistry: organic synthesis and astrochemistry. To tackle both aspects, a multidisciplinary strategy has been exploited and a new, easily accessible synthetic approach to generate stable imine-intermediates in the gas phase and in solution has been introduced. The combination of this formation pathway, based on the thermal decomposition of hydrobenzamide, with a state-of-the-art computational characterization of phenylmethanimine laid the foundation for its first laboratory observation by means of rotational electric resonance spectroscopy. Both E and Z isomers have been accurately characterized, thus providing a reliable basis to guide future astronomical observations. A further characterization has been carried out by nuclear magnetic resonance spectroscopy, showing the feasibility of this synthetic approach in solution. The temperature dependence as well as possible mechanisms of the thermolysis process have been examined.
