Abstract
The unexpected violet colour of P,P′-tetraphenyl-oxalic acid diphosphide (3) stimulated the synthesis of the following derivatives: P,P′-tetra-t-butyl-oxalic acid diphosphide (2), N,P-tetraphenyl-oxalic acid amide phosphide (4) and P, α-triphenyl-glyoxylic acid phosphide (5). The compounds could be prepared by the reaction of the corresponding acyl chlorides with diorganyl-(trimethylsilyl) phosphine; (organyl=t-butyl and phenyl). The electronic transitions of green-blue2 and red5 in the 450–700 nm region are discussed, also theirv C=O in the ir spectrum. These results are interpreted in connection with the molecule structures of2 and3 which have been determined by X-ray crystal structure analysis. In2 the framework P−C(O)−C(O)−P is only slightly distorted from a coplanartrans-position, in3 somewhat more. The bonds at P have the expected pyramidal arrangement. The direction of the lone pairs at the P-atoms, derived from this bond arrangement, is discussed with respect to the electronic transitions in acyl phosphides.
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Literatur
H. J. Becher, D. Fenske undE. Langer, Chem. Ber.106, 177 (1973).
K. Issleib undO. Löu, Z. anorg. allg. Chem.346, 241 (1966).
E. M. Ayerst undJ. R. C. Duke, Acta Cryst.7, 588 (1954).
G. Adiwidjaja undJ. Voß, Chem. Ber.110, 1159 (1977).
M. W. Dougill undG. A. Jeffrey, Acta Cryst.,6, 831 (1953).
Documentation of Molecular Spectroscopy, Formula ListI–X (1967). Butterworth—Verlag Chemie.
D. R. Lide undD. E. Mann, J. Chem. Phys.29., 914 (1958).
J. J. Daly, J. Chem. Soc.1964, 3799.
A. G. Brook, R. Kivisikk undG. E. LeGrow, Canad. J. Chem.43, 1175 (1965).
H. Bock, H. Alt undH. Seidl, J. Amer. Chem. Soc.91, 355 (1969).
D. Fenske, Chem. Ber.112, 363 (1979).
S. Evans, J. C. Green, P. J. Joachim, A. F. Orchard, D. W. Turner undJ. P. Maier, J. Chem. Soc. Faraday Soc. Trans. 2,1972, 905.
L. S. Khaikin, L. G. Andrutskaya, O. E. Grikina undL. V. Vilkow, J. Mol. Structure37, 237 (1977).
H. J. Becher undH. Prokscha, unveröffentlichte Ergebnisse der DissertationH. Prokscha, math.-nat. Fakultät der Universität Münster,1979.
T. Osaki, J. Otera undY. Kawasaki, Bull. Chem. Soc. Japan46, 1803 (1973).
H. Hoffmann undP. Schellenbeck, Chem. Ber.100, 692 (1967).
H. Schumann undL. Rösch, J. Organomet. Chem.55, 257 (1973).
C. Glückmann, Mh. Chem.10, 770 (1889).
J. Acrée, J. Amer. Chem. Soc.35, 393 (1913).
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Becher, HJ., Fenske, D., Langer, E. et al. Struktur und Farbigkeit von P,P′-Tetra-t-butyl-und P, P′-Tetraphenyl-oxalsäurediphosphid und Derivaten. Monatshefte für Chemie 111, 749–759 (1980). https://doi.org/10.1007/BF00903328
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DOI: https://doi.org/10.1007/BF00903328