In:
Zeitschrift für Naturforschung B, Walter de Gruyter GmbH, Vol. 52, No. 12 ( 1997-12-1), p. 1510-1516
Kurzfassung:
Upon heating 1,3,5-trimethylbiuret (1) with trichloromethyldichlorophosphine in the presence of triethylamine, 2-trichloromethyl-1,3,5-trimethyl-1,3,5-triaza-2σ 3 λ 3 -phosphorine-4,6-dione (2) was obtained in good yield. Aside from NMR spectroscopic characterization, compound 2 was investigated by X-ray crystal structure analysis, representing the first case of the solid state characterization of a 2-trihalomethyl-1,3,5-trimethyl-1,3,5-triaza-2σ 3 λ 3 -phosphorine-4,6-dione derivative. The heterocycle presents an envelope conformation with phosphorus out of the plane of the other atoms. Reaction of the monochloromethyl derivative (3) corresponding to 2, with a sterically demanding azide led by oxidation of phosphorus to the stable σ 4 λ 5 -P derivative (4). 2-Hydro-1,3,5-trimethyl-1,3,5-triaza-2-oxo-2σ 4 λ 5 -phosphorine-4,6-dione (5) reacted with p-nitrobenzylidene benzylimine with formation of 6 by insertion of the C=N double bond of the imine into the P-H bond. Intramolecular hydrogen bonding in 6 was observed by 1 H NMR and IR spectroscopy. Reaction of 2-(methylamino)-methyl-1,3,5-trimethyl-1,3,5-triaza-2-oxo-2σ 4 λ 5 -phosphorine-4,6-dione (7) with diethylamino-trimethylsilane led to the corresponding N-trimethylsilylated compound 8. Compound 9. bearing a peptoid group, was formed by reaction of 7 or 8 with 3-(chloroformyl)propionic acid methyl ester. The preferred method of synthesis of 9 is indicated.
Materialart:
Online-Ressource
ISSN:
1865-7117
,
0932-0776
DOI:
10.1515/znb-1997-1212
Sprache:
Englisch
Verlag:
Walter de Gruyter GmbH
Publikationsdatum:
1997
ZDB Id:
2078109-X
ZDB Id:
124635-5
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