The Exchange of Other Organic Compounds containing Oxygen with Water

The Exchange of Other Organic Compounds Containing Oxygen with Water 

Group V Nitrogem and Phosphorus Compounds 1. Nitrogen compounds 

Hydroxylamine (38 R = R = H) does not undergo exchange (Bothner-By and Friedman, 1952) and presumably the mono N- and NN-disubstituted hydroxylamines do not undergo exchange either, but this has not yet been investigated experimentally. 

In a recent study on the hydrolysis of di-isopropylphosphofluoridate (DPP), Samuel and Silver (1963) found that benzohydroxamio acid (38 R = H R = CgHs. CO) had not undergone exchange after 10 min at pH 7 6 at room temperature. In fact, it appears that under all the conditions studied the —OH group does not undergo isotopic exchange. 

The exchange of amine oxides has not yet been examined. Nitromethane (Gragerov and Levit, 1960) and nitrobenzene (Roberts, 1938 Gragerov and Levit, 1960) do not undergo exchange even under very drastic conditions. It should be recalled that exchange with the nitrate ion only occurs in strong acid solution by the reversible formation of a nitronium cation [N02] (Bunton et al., 1952). This mechanism cannot occur in 

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