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New Bifunctional Benzoxazaphosphorinanone Systems
Author(s) -
Lu Yingzi,
Freytag Matthias,
Jones Peter G.,
Schmutzler Reinhard
Publication year - 2002
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/1521-3749(200201)628:1<274::aid-zaac274>3.0.co;2-4
Subject(s) - chemistry , adduct , amide , trimethylsilyl , medicinal chemistry , molecule , trimethylsilyl azide , yield (engineering) , stereochemistry , nuclear magnetic resonance spectroscopy , polymer chemistry , azide , organic chemistry , materials science , metallurgy
The (CH 2 ) n (n = 2, 3)‐bridged, PCl‐functional bis(benzoxazaphosphorinanone) derivatives, 3 a and 3 b , were prepared in high yield by the reaction of the salicylic acid amide derivatives, 2 a and 2 b , with phosphorus trichloride. Cyclocondensation of 3 a and 3 b with the bis(trimethylsilyl)ethers, 4 a – 4 c , furnished the symmetrical benzoxazaphosphorinanone derivatives, 5 a – 5 f , in moderate yield. 5 a – 5 f involve a nine‐membered ring, made up of carbon, nitrogen, phosphorus, and oxygen, as a central feature. Oxidation of 5 a – 5 f with the urea‐hydrogen peroxide adduct, (H 2 N) 2 C(:O) · H 2 O 2 , gave rise to the corresponding phosphoryl compounds, 6 a – 6 f . All new compounds were characterized by NMR spectroscopy, mass spectrometry, and elemental analysis. For compound 6 e an X‐ray crystal structure determination was conducted; the two formally identical halves of the molecule differ appreciably in the torsion angles in the region P–O–C (naphthyl).