By K. Dimroth
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Good resolution of the hyperfine structure of the signals was not obtained. So far chemical reactions have been performed only with the cation radicals as intermediates. 3. Oxidation with Oxygen, Nitric Acids, Hydrogen Peroxide, Halogens and Aryldiazonium Salts a) Oxidation with Oxygen ~) Air Oxidation in the Dark. 6-triphenyl or higher substituted Aa-phosphorins are rather stable to air. p. 162-165 ~ and 225 ~ precipitate, as Vogel has found 70). The constitution of the two compounds was published by us with some reservations.
176-178 ~ on esterification with diazomethane, leads to a mixture of two diastereoisomeric esters, 89 E and 89 Z, which could be separated by thinlayer chromatography but not crystallized. The most interesting point is the observation of differences in the H - H coupling constants of the protons at C - 2 and C - 3 . From this we suppose that the conformation for the two stereoisomers with respect to an equatorial position of all three tert-butyl groups is not maintained (in contrast to the 4-hydroxy-phosphinic acid series).
These signals are due to the two equivalent protons at C - 3 and C - 5 which are split into a doublet by phosphorus, as can be seen by inspection of the NMR spectrum of tds-pentadeuterophenyl-;~a-phosphorin (Fig. 9 and 10). -- 8 I I 7 t I 6 I l v 5 PP~d" ) Fig. 9. 6-h3-triphenylphosphorin22 8 7 6 5 P~(i ) Fig. 10. 3-Phosphorins are thus "'aromatic" in the sense that they show a clear ring-current effect. ta-phosphorin 24 in CDCI3 is quite similar in that the two ring protons absorb at ~i = 7,77 ppm with a coupling constant of J p - c - C - H = 6 Hz.