Synthesis of tetraphenylphosphonium (thio)phosphorylthiobenzamides and hydrolytic degradation to Ph3P=O, H2S and phosphoryl(thio)benzamides: A route for crystal design of PhC(X)NHP(O)(OiPr)2 (X=S, O)

Reactions of the sodium salts of PhC(S)NHP(Y)(OiPr)2 (Y=S, HLI; O, HLII) with PPh4Br in 96% aqueous EtOH leads to the corresponding compounds PPh4LI,II. The structures of these compounds were investigated by IR, 1H, 31P{1H} NMR spectroscopies; their compositions were examined by microanalysis. Recrystallization of PPh4LI,II from EtOH/H2O solution (1:1, v/v) leads to the formation of HLII and PhC(O)NHP(O)(OiPr)2 (HLIII), respectively. The crystal structures of HLII,III are reported and compared with the previously reported polymorphs.