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.

Reactions of the sodium salts of PhC(S)NHP(Y)(OiPr)2 (Y=S, HLI; O, HLII) with PPh4Br give the corresponding compounds PPh4LI,II. Recrystallization of PPh4LI,II from EtOH/H2O solution 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.Figure optionsDownload as PowerPoint slideHighlights
► Tetraphenylphosphonium salts of PhC(S)NHP(Y)(OiPr)2 (Y=S, O) are reported.
► The compounds were examined by IR, 1H and 31P{1H} NMR spectroscopy.
► New crystal polymorphs of PhC(X)NHP(O)(OiPr)2 (X=S, O) were obtained.