Lewis and Bronsted basicity of phosphine-diazomethane derivatives

The compounds EtOC(=O)CHNNPR3(R = Ph 1, Cy 2, tBu 3) were prepared via the reactions of the diazomethane and a phosphine. In subsequent reactions with B(C6F5)(3), the compounds 2 and 3 are shown to exhibit Lewis basicity at the carbonyl oxygen affording EtOC(=O(B(C6F5)(3)))CHNNPR3(R = Cy 5, tBu 6). Reactions of 5 and 6 with water or phenol illustrated the Bronsted basicity at the nitrogen atom adjacent phosphorus, affording the compounds, [EtOC(=O)CHNNHPR3][HOB(C6F5)(3)] (R = Cy 7, tBu 8) and [EtOC(=O)CHNNHPR3][PhOB(C6F5)(3)] (R = Cy 9, tBu 10), respectively. The formulation of these products is confirmed via spectroscopic and crystallographic studies, and insight is garnered from computations.