840500-40-5Relevant academic research and scientific papers
Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents
Hudson, Harry R.,Tajti, ádám,Bálint, Erika,Czugler, Mátyás,Karaghiosoff, Konstantin,Keglevich, Gy?rgy
, p. 1446 - 1455 (2020/03/16)
A series of N-benzhydryl protected α-aminophosphonates with α-phenyl, α-(1-naphtyl), α-(9-anthryl) or α-(1-pyrenyl) substituents was synthesized by the Kabachnik–Fields condensation of diphenylmethylamine (benzhydrylamine), the corresponding aryl aldehyde and a dialkyl phosphite under MW irradiation. X-ray studies performed at low temperatures for a few of these α-aminophosphonates confirmed the presence of unusually short intramolecular Cα–Hδ+ ··· δ+H–Cperi contacts.
Extremely short H?H distances and intermolecular hydrogen-bonding patterns of dialkyl α-aryl-α-(diphenylmethylamino)methanephosphonates
Hudson, Harry R.,Czugler, Mátyás,Lee, Rosalind J.,Woodroffe, Thomas M.
, p. 469 - 477 (2016/04/09)
Single crystal X-ray diffraction studies of four N-benzhydryl protected diethyl α-amino-α-arylmethanephosphonates (aryl = phenyl, 1-naphthyl, 1-anthryl, and 1-pyrenyl) reveal several distinct types of hydrogen bonding, leading to the formation of (a) dime
Unexpected non-stability of aminophosphonates: Limitation of their synthesis using diphenylmethylamine procedure
Zon,Miziak,Rychlewski,Gancarz
, p. 2023 - 2030 (2008/09/18)
New diethyl 1-diphenylmethylaminoalkylphosphonates from aldehydes, ketones, diphenylmethylamine and diethyl phosphite were obtained. Their stability in acidic media as determined by 31P NMR spectroscopy strongly depends on the basicity of the nitrogen atom. The bulky N-substituent can drastically decrease the stability of the ester during acidic hydrolysis leading to decomposition products in the retro Kabachnik-Fields like reaction.
1-Amino-1-aryl- and 1-amino-1-heteroaryl-methanephosphonic acids and their n-benzhydryl-protected diethyl esters: Preparation and characterization
Hudson, Harry R.,Lee, Rosalind J.,Matthews, Ray W.
, p. 1691 - 1709 (2007/10/03)
N-Benzhydryl-protected diethyl esters of 1-amino-1-aryl- (phenyl, cumyl, p-dimethylaminophenyl, piperonyl, 1′-naphthyl, 9′-anthryl, 1′-pyrenyl) and 1-amino-1-heteroaryl- (furyl, 2′-thienyl, 3′-thienyl, 2′-pyrrolyl)-methanephosphonic acids, prepared by the
