1-AMINO-1-ARYL- AND 1-AMINO-1-HETEROARYL-METHANEPHOSPHONIC ACIDS AND THEIR N-BENZHYDRYL-PROTECTED DIETHYL ESTERS: PREPARATION AND CHARACTERIZATION

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 179; no. 9; pp. 1691 - 1709
• Main Authors: Hudson, Harry R., Lee, Rosalind J., Matthews, Ray W.
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis Group 01.09.2004; Taylor & Francis
• Subjects: Aminophosphonate; aminophosphonic acids; aryl; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; heteroaryl; mass spectrometry; NMR; Physical Sciences; Science & Technology; aryl; heteroaryl; 1-AMINOPHOSPHONIC ACIDS; SHIFTS; EQUIVALENCE; PHOSPHORUS-COMPOUNDS; BIPHENYLENE; NMR; aminophosphonate; aminophosphonic acids; SPECTROSCOPY; BEARING HETEROCYCLIC MOIETY; BOMBARDMENT MASS-SPECTROMETRY; CARBON-13 MAGNETIC RESONANCE; mass spectrometry; DERIVATIVES
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426500490466274

n-Benzhydryl-protected diethyl[3.3pc] 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 addition of diethyl phosphite to the corresponding benzhydryl imines, have been isolated, purified, and characterized. The presence of chiral α -carbon and prochiral phosphorus in these esters gives rise to complicated features in their NMR spectra, which are discussed. Hydrolysis of the crude 1-aryl compounds in situ gave modest yields of the corresponding aminophosphonic acids (except for 1′-pyrenyl). Of the 1-heteroaryl derivatives, only the 2′-thienyl compound gave the expected aminophosphonic acid; in other cases, alternative[-18pc] modes of decomposition may occur under hydrolytic conditions. NMR and mass spectral data are given for all products.