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Phosphine Carboxylate - Probing the Edge of Stability of a Carbon Dioxide Adduct with Dihydrogenphosphide.

We present a new adduct of carbon dioxide with dihydrogenphosphide, that may be prepared either by direct reaction of NaPH 2 with carbon dioxide or by hydrolysis of the phosphaethynolate ion (PCO - ). In this latter transformation, a new mechanism is proposed for the electrophilic reactivity of the phosphaethynolate ion. The resulting anion is shown to be a weak but stable adduct of carbon dioxide, reminiscent of transition-metal carbon dioxide complexes. Protonation to form phosphine carboxylic acid (PH 2 COOH) and functionalization to form esters is shown to increase the strength of the P-C interaction, allowing for comparisons to be drawn between this species and the analogous carbamic (NH 2 COOH) and carbonic acids (H 2 CO 3 ). Functionalization of the oxygen atom is found to stabilize the phosphine carboxylate while also allowing solubility in organic solvents whereas phosphorus functionalization is shown to facilitate decarboxylation. Substituent migration occurs in some cases.